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Villas and apartments in Berkshires, MA

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All 105 Rentals in Berkshires
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From
€407
Per Night
1 / 23
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Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
From
€81
Per Night
1 / 13
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Becket
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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From
€407
Per Night
1 / 19
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Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 15
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From
€183
Per Night
1 / 14
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Hancock
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details 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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From
€163
Per Night
1 / 8
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
€204
Per Night
1 / 7
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
€204
Per Night
1 / 10
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Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details 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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From
€118
Per Night
1 / 16
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Hancock
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details 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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From
€407
Per Night
1 / 11
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Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly... View all property information
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From
€244
Per Night
1 / 12
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 1
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • x
About this property
Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington... View all property information
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4 of 5 stars Reviewed 21 July 2014
The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although...
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From
€110
Per Night
1 / 11
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Richmond
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details 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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From
€102
Per Night
1 / 6
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West Stockbridge
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
€1,055
Per Week
1 / 16
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Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Private Beach
  • Satellite TV
  • 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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From
€106
Per Night
1 / 20
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Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • 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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From
€59
Per Night
1 / 27
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Safe
  • Sauna
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The Two-Bedroom Condos are the ultimate Hancock, Massachusetts vacation retreat. Apart from two ultra-spacious private bedrooms and two oversized bathrooms, take advantage of the washer and dryer and fully equipped kitchen for additional travel savings. Create fun filled memories just minutes from... View all property information
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4 of 5 stars Reviewed 19 September 2014
What a pleasant and wonderful stay. This is the second Wyndham resort we have stayed at. We had asked for a room on the top floor with a view and that was exacly what we got...
4 of 5 stars Reviewed 19 August 2014
The condo has a full kitchen and living room, making it pleasant to gather with family and/or friends in the evening or on a rainy day.
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From
€98
Per Night
1 / 10
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North Adams
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
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. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! Animals are welcome... I have a cat that I usually keep there... The master bedroom has an extended queen sleep number bed and the spare... 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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From
€139
Per Night
1 / 35
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North Egremont
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • 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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From
€146
Per Night
1 / 16
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Sauna
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
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4 of 5 stars Reviewed 25 October 2014
Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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From
€143
Per Night
1 / 10
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Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details 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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From
€143
Per Night
1 / 12
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Monterey
Studio, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. View all property information
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From
€407
Per Night
1 / 32
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Stockbridge
4 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
€244
Per Night
1 / 25
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Lee
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details 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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From
€94
Per Night
1 / 35
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Charlemont
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (100) 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 26 November 2014
Cavalier Cottage is a gem for people and dogs. My family and I were impressed by the amount of detail put into it---- it had everything you can think of- gourmet tea and...
5 of 5 stars Reviewed 19 November 2014
The Cavalier Cottage is a nice, clean and bright studio cottage. Pat is the perfect host, providing us with warm scones and orange juice every morning. She welcomed us and our 2...
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From
€306
Per Night
1 / 33
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Lee
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
Details 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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From
€204
Per Night
1 / 9
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Tyringham
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
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From
€367
Per Night
1 / 17
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
€224
Per Night
1 / 32
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Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details 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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From
€204
Per Night
1 / 12
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West Stockbridge
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Details Reviews (8) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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 28 October 2014
Our group of 9 friends stayed here for two nights in late October. Everyone was pleased with the accomodations. The house is close to Stockbridge, Lee, and Lenox. It is nestled in...
5 of 5 stars Reviewed 31 August 2014
We were a group nine. We found the house to have a rustic charm complete with hardwood floors and exposed beams in the walls and ceilings. We tended to congregate in the living...
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From
€204
Per Night
1 / 16
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North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Mountain Views
  • Private Fishing...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
€106
Per Night
1 / 8
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Hinsdale
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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From
€122
Per Night
1 / 4
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Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details 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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From
€183
Per Night
1 / 16
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Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
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Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
€187
Per Night
1 / 4
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details 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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From
€489
Per Night
1 / 33
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Great Barrington
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
€367
Per Night
1 / 20
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Richmond
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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From
€379
Per Night
1 / 27
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Great Barrington
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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...
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From
€163
Per Night
1 / 11
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Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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From
€41
Per Night
1 / 6
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Monterey
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
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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From
€407
Per Night
1 / 18
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Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
€128
Per Night
1 / 9
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 1
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc..... View all property information
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From
€530
Per Night
1 / 22
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Great Barrington
4 Bedrooms, 6 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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From
€147
Per Night
1 / 15
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Sandisfield
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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From
€326
Per Night
1 / 24
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Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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From
€122
Per Night
1 / 6
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Savoy
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
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From
€183
Per Night
1 / 16
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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From
€204
Per Night
1 / 21
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Monterey
5 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
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From
€106
Per Night
1 / 16
Payment Protection
Stockbridge
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
New Listing on Tripadvisor. One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center.... View all property information
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From
€122
Per Night
1 / 15
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Dalton
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Cottage at Holiday Farm is a gorgeous place to spend the month, week or a mini-break weekend. Centered in the heart of a real, working farm there are miles of wooded trails and farm roads right outside the door. You can wander the farm, enjoy seasonal sports activities from cross-country skiing... View all property information
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From
€183
Per Night
1 / 21
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Lee
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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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From
€204
Per Night
1 / 13
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • 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
Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room... View all property information
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