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Villas and Holiday Rentals in Berkshires, MA

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    1 / 7
    5 of 5 stars (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 10
    South Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 18
    5 of 5 stars (11) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • 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
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 16 July 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
    5 of 5 stars Reviewed 1 September 2015
    My husband and I plus our two dogs recently took one last family vacation before our first son arrives later this year. We were looking for a private and peaceful place where we...
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    1 / 14
    5 of 5 stars (2) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • Shared Indoor Pool
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    • Pet-friendly
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    • x
    About this property
    220 acres with tennis, indoor & outdoor pools, yoga studio, gym and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 2 weeks ago
    The Playhouse is a magical place to connect with friends and family. There are a half dozen living spaces that offer anything from quiet reading areas with a view, to 40 person...
    5 of 5 stars Reviewed 2 weeks ago
    I didn't want to leave. The view from the picture window is breathtaking. The home has more space than even our large group could fill. If you are a yogi, you can enjoy your own...
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    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Balcony
    • DVD Player
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    • Central Heating
    • Porch
    • Mountain Views
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    • Pet-friendly
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    • 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
    Location Information
    Lenox, Berkshires 01240
    4 of 5 stars Reviewed 8 July 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 3 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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    1 / 10
    4.5 of 5 stars (15) Very good
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. We are about 8 minutes away from Jiminy Peak and... View all property information
    Location Information
    Lanesboro, Berkshires 01237
    4 of 5 stars Reviewed 3 weeks ago
    Private and peaceful. Located where many cultural activities are available.Caring hosts.Our 2nd year!
    5 of 5 stars Reviewed 12 February 2016
    My boyfriend and I celebrated my birthday weekend at the cottage. We had a rough start the day we were to arrive and Cheryl was just wonderful and so understanding. We were...
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    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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    1 / 25
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Patio
    • Grill
    • Mountain Views
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
    Location Information
    Stockbridge, Berkshires 01262
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    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Waterfront
    • Porch
    • Mountain Views
    • Central Heating
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    North Adams, Berkshires 01247
    1 / 16
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    1 / 12
    4 of 5 stars (1) Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed 1 week ago
    We stayed at Jo-Anne's cottage for a week in mid-July. Wasn't sure what to expect as the place had no reviews. Our hostess made us feel at home right away and made a major...
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    1 / 20
    5 of 5 stars (25) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 9 May 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
    5 of 5 stars Reviewed 30 March 2016
    Some girlfriends and I decided to meet up for a weekend and found this wonderful home which was super convenient for all of us - some coming from MA others from upstate NY. When...
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    1 / 11
    3.5 of 5 stars (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed 5 weeks ago
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 stars Reviewed 14 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223
    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 28 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 / 19
    5 of 5 stars (2) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    • Air Conditioning
    • Mountain Views
    • Satellite TV
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    • Skiing: Property Is...
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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 (about a 10 minute walk)!!! Animals are welcome if needed. The master... View all property information
    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 11 September 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    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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    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 10
    5 of 5 stars (4) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 4 weeks ago
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for our...
    5 of 5 stars Reviewed 16 May 2016
    Tucked away down a country road, farm fresh eggs for breakfast, wonderful rustic cottage details everywhere, Apple Cottage does not disappoint! The cottage easily accommodated 7...
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    1 / 22
    Lenox
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • Satellite TV
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    • Mountain Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the... View all property information
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    Lenox, Berkshires 01240
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    1 / 32
    5 of 5 stars (4) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    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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    Becket, Berkshires 01223
    5 of 5 stars Reviewed 4 days ago
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches & dinners...
    5 of 5 stars Reviewed 14 May 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    1 / 46
    5 of 5 stars (1) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 25 | Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Satellite TV
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed 30 May 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    1 / 24
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Porch
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Lee, Berkshires 01238
    1 / 22
    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
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    Otis, Berkshires 01255
    1 / 7
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
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    Lee, Berkshires 01238
    1 / 14
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Lenox, Berkshires 01240
    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    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
    Location Information
    Lee, Berkshires 01238
    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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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2" would be... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 16 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    1 / 8
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
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    Lenox, Berkshires 01240
    1 / 10
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Mountain Views
    • Outdoor Dining Area
    • Balcony
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    • Hot Tub
    • Internet Access
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
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    Lee, Berkshires 01238
    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • 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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    Richmond, Berkshires 01254
    3 of 5 stars Reviewed 26 October 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
    5 of 5 stars Reviewed 7 September 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also quiet...
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    1 / 52
    5 of 5 stars (8) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Grill
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    • Waterfront
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,... View all property information
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    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 19 July 2016
    From the moment we turned off the beautiful country road and into River Song's driveway my wife and I sensed we were in for a treat. Barbara and Phillip came out to meet us and...
    5 of 5 stars Reviewed 7 October 2015
    My husband and I were looking for a relaxing getaway for a long weekend. We chose the River Song and were not disappointed. The suite is beautifully and comfortably furnished...
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    1 / 37
    5 of 5 stars (141) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Satellite TV
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    • Secure Parking
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 the... View all property information
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    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed 2 weeks ago
    Places like this one are rare. The hostess, the facility itself, and the setting are all beyond compare. Patricia is warm and welcoming, friendly but never intrusive. She thinks...
    5 of 5 stars Reviewed 4 weeks ago
    I found Cavalier Cottage because I was looking for a place to stay where I could bring my two dogs. What I found was a delight; a cottage that I would happily return to even...
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    1 / 20
    5 of 5 stars (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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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    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed 31 May 2016
    This home is meticulous, charming, cozy, comfortable and relaxing. We thoroughly enjoyed the backyard and spent hours just visiting with each other over a warm fire while the...
    5 of 5 stars Reviewed 29 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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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Hot Tub
    • Mountain Views
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A 1/4 mile driveway thru the woods takes you to 35 acres, and this beautiful contemporary home on your own PRIVATE small swimming and fishing lake. (2.5 acres) 3 br, 3full baths, and sofa bed in sunroom. .2500 sq feet, lots of windows and views from everywhere. (see pictures) Open floor plan... View all property information
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    Stockbridge, Berkshires 01260
    1 / 6
    5 of 5 stars (3) Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • 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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    Savoy, Berkshires 01256
    5 of 5 stars Reviewed 3 February 2016
    What a quaint and absolutely lovely place to have spent the weekend. The quiet and peaceful surroundings along with the gorgeous wood interior made for a very homey and...
    5 of 5 stars Reviewed 9 December 2015
    Words can't begin to describe how amazing this rental is! My husband and I were married in November of 2014. Being a teacher, we couldn't go away for a long honeymoon so we...
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    1 / 27
    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 | Quick View
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    • Patio
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    • Central Heating
    • Mountain Views
    • Skiing: Property Is...
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a... View all property information
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    North Adams, Berkshires 01247
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 9 September 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Sauna
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    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 18 February 2016
    My family and I come here every February to snowboard/ski. My boys are in their 20's and they still want to come here with the family and have fun. This year though my husband...
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    • Mountain Views
    • DVD Player
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    • Porch
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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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    Great Barrington, Berkshires 33304
    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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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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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    Hancock, Berkshires 01237
    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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    1 / 10
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
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    West Stockbridge, Berkshires 01266
    1 / 6
    Lee
    1 Bedroom, 3 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    This is the second floor of the barn. Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot pot and coffeemaker. Bathroom has... View all property information
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    Lee, Berkshires 01238
    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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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    Lee, Berkshires 01238
    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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    1 / 10
    5 of 5 stars (1) Excellent
    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers... View all property information
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    Richmond, Berkshires 01254
    5 of 5 stars Reviewed 14 June 2016
    My wife and I stayed here for a week in June. The hosts/owners are new to the rental business, but were eager to make sure everything was in order for us. The house is very well...
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    West Stockbridge, Berkshires 01266
    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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    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Balcony
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    • Air Conditioning
    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
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    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    1 / 9
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • 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
    Location Information
    Tyringham, Berkshires 01264
    1 / 21
    5 of 5 stars (21) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Porch
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    • Central Heating
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    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lenox, Berkshires 01240
    5 of 5 stars Reviewed 20 January 2016
    My friends and I loved the Gartner home. It was conveniently located to downtown Lenox, cozily furnished and spotlessly clean. The eat in kitchen was well stocked with everything...
    4 of 5 stars Reviewed 16 October 2015
    We were here during the 2015 foliage season. Absolutely beautiful. The house was very roomy and very comfortable. Has all the amenities you need in kitchen and other rooms...
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