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Villas and Holiday Rentals in Berkshires, MA

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    All 105 Rentals in Berkshires
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    €403
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    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield
    4 Bedrooms / 3 Bathrooms / Sleeps 15
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    €169
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    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €1,522
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    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    €224
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
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    5 of 5 stars Reviewed 20 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    €124
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    1 / 16
    5 of 5 stars (9) Excellent
    Becket
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge... View all property information
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    5 of 5 stars Reviewed 17 January 2014
    We had a wonderful time in the Berkshires, and this cottage was the central part of our weekend. The house was superb and extra clean, with everything provided. Views were...
    5 of 5 stars Reviewed 2 October 2013
    Excellent spot for a quiet retreat. Located on a nice pond with just a few neighbors we never even saw or heard. The cottage has all the essentials. Very clean and inviting...
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    €157
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    1 / 16
    Becket
    4 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating... View all property information
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    €130
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
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    5 of 5 stars Reviewed 16 October 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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    €201
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    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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    €269
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    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter... View all property information
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    5 of 5 stars Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 27 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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    €133
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    1 / 44
    5 of 5 stars (5) Excellent
    North Egremont
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,... View all property information
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    5 of 5 stars Reviewed 12 September 2014
    I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
    5 of 5 stars Reviewed 4 September 2014
    Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
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    €157
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    1 / 10
    5 of 5 stars (12) Excellent
    Lanesboro
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family... View all property information
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    5 of 5 stars Reviewed 8 July 2014
    We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
    5 of 5 stars Reviewed 30 May 2014
    We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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    €178
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    1 / 10
    5 of 5 stars (12) Excellent
    Great Barrington
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
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    5 of 5 stars Reviewed 17 August 2014
    We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
    5 of 5 stars Reviewed 22 July 2014
    My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
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    €205
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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    4 of 5 stars Reviewed 11 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    €89
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    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,... View all property information
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    5 of 5 stars Reviewed 3 November 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed 29 June 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
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    €1,075
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    1 / 16
    Great Barrington
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
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    €269
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    €116
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    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an... View all property information
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    5 of 5 stars Reviewed 6 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    €134
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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
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    5 of 5 stars Reviewed 17 June 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    €246
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    1 / 32
    5 of 5 stars (1) Excellent
    Becket
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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    5 of 5 stars Reviewed 29 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    €358
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    1 / 12
    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    €322
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    1 / 33
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
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    4 of 5 stars Reviewed 27 September 2014
    We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
    5 of 5 stars Reviewed 3 September 2014
    This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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    5 of 5 stars (108) Excellent
    Charlemont
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (108) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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    5 of 5 stars Reviewed 30 March 2015
    Beyond all expectations, we relaxed in royal blue, in quiet and comfortable surroundings -- a place to which we plan to return again, to enjoy in other seasons, to fully...
    5 of 5 stars Reviewed 24 March 2015
    This cottage is a great place to stay, especially for those traveling with pets. Pat is very hospitable and there is plenty of privacy. We definitely need more people & places...
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    €313
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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    5 of 5 stars Reviewed 5 February 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
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    €224
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock... View all property information
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    4 of 5 stars Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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    €128
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    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
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    5 of 5 stars Reviewed 1 February 2015
    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
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    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
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    5 of 5 stars Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    5 of 5 stars (4) Excellent
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    4 of 5 stars Reviewed 24 October 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
    5 of 5 stars Reviewed 30 September 2013
    We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
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    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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    Monterey
    1 Bedroom / 1 Bathroom / Sleeps 1
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    We rent our house for a full winter season from November through March. You can enjoy all holidays, school breaks, weekends during the winter in your own winter wonderland. Contact us for all details. Walk to charming 200 year old Monterey with library, playground, playing fields, ice skating... View all property information
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    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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    5 of 5 stars Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    5 of 5 stars (3) Excellent
    Lee
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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    5 of 5 stars Reviewed 19 April 2015
    This is a very special place to stay in the Berkshires! Not only is its location perfect for getting to Tanglewood, Jacobs Pillow, Stockbridge, and most other Berkshires...
    5 of 5 stars Reviewed 17 April 2015
    Friends and I gathered for two days at this rental. It was everything that we could have desired and more: great location, nearby walks, a roomy and perfectly maintained rental...
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    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    5 of 5 stars Reviewed 12 June 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    4.5 of 5 stars (13) Very good
    Monterey
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Tyringham
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Balcony
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting.... View all property information
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    5 of 5 stars Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
    5 of 5 stars Reviewed 25 August 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    5 of 5 stars Reviewed 4 December 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed 18 July 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
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    5 of 5 stars Reviewed 30 November 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
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    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Fireplace
    • Grill
    • Mountain Views
    • Private Fishing...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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    5 of 5 stars Reviewed 16 August 2014
    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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    5 of 5 stars (7) Excellent
    Hancock
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
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    5 of 5 stars Reviewed 12 October 2014
    Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
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    5 of 5 stars (13) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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    5 of 5 stars Reviewed 20 April 2015
    We spent 3 nights here, 2 with sons, daughters in law and four grandchildren. There were plenty of bedroom plus a foldout couch, and the kitchen was very well equipped. One of...
    5 of 5 stars Reviewed 24 February 2015
    We just spent a wonderful week staying at the Berkshire Farmhouse. The house was exactly as pictured, and Elaine was a warm and friendly host. She gave us a lot of great...
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    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms / 1 Bathroom / Sleeps 7
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    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
    • x
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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    5 of 5 stars Reviewed 3 January 2015
    Ski trip in Berkshires and this place was perfect. Gave us nice options to do on off days. Debra was great with any issues that came up and was very helpful and responsive...
    5 of 5 stars Reviewed 22 October 2014
    We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
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    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    3 of 5 stars (1) Average
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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    3 of 5 stars Reviewed 31 July 2014
    Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
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    Hancock
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    • ?
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
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    3 of 5 stars Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed 5 January 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
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    3.5 of 5 stars (3) Average
    Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc. View all property information
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    3 of 5 stars Reviewed 14 October 2014
    We were in the older condos that need new furnishings, tvs, appliances, etc. I recommend trying to get into the newer condos; but not the older units; thus my rating below...
    4 of 5 stars Reviewed 14 July 2014
    My wife and I spent a restful week at The Oak and Spruce resort in the Berkshires. The unit was roomy and had a large master bedroom with jacuzzi and shower.The second bedroom had...
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    Hinsdale
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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    Charlemont
    5 Bedrooms / 3 Bathrooms / Sleeps 14
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    • Grill
    • Internet Access
    • Mountain Views
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
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    Granville
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Balcony
    • Dishwasher
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Wheelchair access
    • Elder access
    • x
    About this property
    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two... View all property information
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