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Pet Friendly Holiday Rentals in Berkshires, MA

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    1 / 25
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 21
    5 of 5 bubbles (3) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    1 / 10
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 12
    4 of 5 bubbles (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 bubbles Reviewed 12 August 2016
    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 / 25
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Parking
    • Patio
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    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • 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
    5 of 5 bubbles Reviewed 28 November 2016
    Me & my son Josh had a lovely stay at the cottage. Ruth was very pleasant, the place was clean and the location was perfect. We were provided with wood for fire, the kitchen has...
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    1 / 8
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles 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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    1 / 20
    5 of 5 bubbles (26) 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
    4 of 5 bubbles Reviewed 2 January 2017
    This Berkshire Farmhouse worked out great for our 3 family reunion. The house was clean, stocked with plenty of blankets and towels, as well as many other amenities. The owner...
    5 of 5 bubbles 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...
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    1 / 17
    5 of 5 bubbles (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Parking
    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 12 October 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    5 of 5 bubbles 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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    1 / 16
    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
    About this property
    220 acre Fox Hollow Estate with 1000 feet of Lake Front on Laurel Lake. 8 Person Hot tub on deck. Fabulous deck fire pit, outdoor furniture and gas grill. Fireplace to warm up by. High ceilings, open living concept. 2400 sq. feet with 4 BR's on main level each with private bath, TV and DVD. 3... View all property information
    Location Information
    Lenox, Berkshires 01240
    1 / 30
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 23 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    1 / 37
    5 of 5 bubbles (150) 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
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    • 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
    Location Information
    Charlemont, Berkshires 01339
    5 of 5 bubbles Reviewed 4 weeks ago
    Its a lovely B & B that was extremely welcoming to me and my 100 pound pup. The cottage is beautifully decorated, clean and offers large living area with plenty of seating and a...
    5 of 5 bubbles Reviewed 23 December 2016
    My husband and I had a three-day, out-of-this-world-relaxing stay at Cavalier Cottage. Not only were we able to bring our two rescue companions, but the inside of this adorable...
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    1 / 18
    5 of 5 bubbles (11) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
    • Parking
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles 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 bubbles 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 / 7
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Lee, Berkshires 01238
    1 / 23
    5 of 5 bubbles (2) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is...
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • 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 bubbles 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 bubbles 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 / 21
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining.... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 46
    5 of 5 bubbles (1) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Satellite TV
    • Patio
    Suitability
    • 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 bubbles 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 / 31
    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 | Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is...
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    • 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
    Location Information
    North Adams, Berkshires 01247
    1 / 32
    5 of 5 bubbles (4) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223
    5 of 5 bubbles Reviewed 21 August 2016
    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 bubbles 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 / 14
    4.5 of 5 bubbles (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Hancock, Berkshires 001237
    1 / 7
    5 of 5 bubbles (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of... View all property information
    Location Information
    North Adams, Berkshires 01247
    5 of 5 bubbles Reviewed 25 August 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    5 of 5 bubbles Reviewed 24 August 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in the...
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    1 / 25
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Private Indoor Pool
    • Hot Tub
    • Air Conditioning
    • Sauna
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Lenox, Berkshires 01240
    1 / 13
    Granville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the... View all property information
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    Granville, Berkshires 01034
    1 / 10
    4 of 5 bubbles (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
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    Great Barrington, Berkshires 01230
    1 / 20
    5 of 5 bubbles (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • 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
    Location Information
    Pittsfield, Berkshires 01201
    5 of 5 bubbles 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 bubbles 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 / 24
    5 of 5 bubbles (10) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy all the Berkshires has to offer in the recently restored and renovated 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 schoolhouse has been... View all property information
    Location Information
    Lee, Berkshires 01260
    5 of 5 bubbles Reviewed 12 September 2016
    This review is long overdue. I stayed here with my family of 5 plus grandparents. The house is postcard beautiful and very well-maintained. There was plenty of room for all of...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
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    • 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
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 bubbles 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 / 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 / 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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    • Smoking allowed
    • 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 / 17
    Williamstown
    4 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
    • Wi-Fi
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    • Patio
    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Lots of space, great yard, walk to everything: restaurants, museums, Williams College, theater, night life, etc. Plus, nearby ski and tubing areas. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally... View all property information
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    Williamstown, Berkshires 01267
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
    Location Information
    Stockbridge, Berkshires 01262
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    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
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    Stockbridge, Berkshires 01262
    1 / 16
    4.5 of 5 bubbles (18) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Monterey, Berkshires 01245 0933
    5 of 5 bubbles Reviewed 18 November 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
    4 of 5 bubbles Reviewed 10 November 2015
    When looking for a house to rent in the Berkshires I began with spots in the towns. However we chose this place due to the reasonable price. As it turned out we liked the remote...
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    1 / 45
    Lee
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Chanterwood is an expansive, light-filled modern home with the luxuries one expects today in a lakefront estate blended with the comfort, casualness and intimacy of its' 100-year old Inn heritage. Sited on 12 acres with 300 feet of private, pristine shoreline, private sandy beach and lawns... View all property information
    Location Information
    Lee, Berkshires 01238
    1 / 15
    Sheffield
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Private, 13 Acres, In-Ground Heated Pool, 4 Bdrms, 3&1/2 Baths, Home Office This completely renovated & restored horse barn has been carefully designed, decorated and conceived to guarantee our guests a private & carefree vacation. The main house has 4 bdrms w/ 3&1/2 baths. There is also a... View all property information
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    Sheffield, Berkshires 01257
    1 / 18
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey.... View all property information
    Location Information
    Great Barrington, Berkshires
    1 / 25
    5 of 5 bubbles (11) Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Outdoor Dining Area
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    • Central Heating
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 bubbles Reviewed 16 October 2016
    Just got back from our stay at the Wolfs Den and i already cant wait to go back! Its a great place for a friends trip or a family trip! Nestled in the woods with a beautiful deck...
    5 of 5 bubbles Reviewed 24 August 2016
    Thanks Kevin for renting your place to us. We love it there!!! The place is nice and cozy for our family. Everything we needed was all there. My family have a great time there...
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    1 / 20
    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Richmond, Berkshires 01254
    1 / 28
    5 of 5 bubbles (2) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    BREAKING NEWS: Cavalier Cottage has received, for the 2nd consecutive year, two distinguished awards as 'Top Vacation Rental' and 'Rated Excellence' by FlipKey, a division of TripAdvisor. In their own words... 'Congratulations! Based on exceptional guest reviews and an impressive listing, you... View all property information
    Location Information
    Charlemont, Berkshires 01370
    1 / 13
    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Balcony
    • Air Conditioning
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    • Mountain Views
    • Satellite TV
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors... View all property information
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    Sheffield, Berkshires 01257
    1 / 24
    5 of 5 bubbles (28) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Satellite TV
    • Mountain Views
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Lee, Berkshires 01260
    5 of 5 bubbles Reviewed 13 January 2017
    We found this online, and you never know what you're getting until you arrive. What we found was amazing - a very old schoolhouse, completely renovated. Everything works...
    5 of 5 bubbles Reviewed 13 March 2016
    Did a 2-night, 3-day get-away with college friends here. It was a perfect location for it. The home is spacious, beautifully renovated (the mortis and tenon beam construction...
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    1 / 6
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest... View all property information
    Location Information
    Lenox, Berkshires 01240