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Holiday Rentals in Berkshires, MA

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    Travellers to Berkshires are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    North Adams
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 23
    5 of 5 stars (2) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 50
    5 of 5 stars (7) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
    • Central Heating
    • DVD Player
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    • Porch
    • Outdoor Dining Area
    • Wi-Fi
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    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
    Location Information
    Lee, Berkshires 01238
    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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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ***Price and availability subject to change without notice*** Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides a vast array of cultural and historic attractions. Visit... View all property information
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    Hancock, Berkshires 01237
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 | Quick View
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    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a... View all property information
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    Lee, Berkshires 01238
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
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    • Mountain Views
    • Satellite TV
    • Grill
    • Outdoor Dining Area
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    • Pet-friendly
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    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . 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
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    Lee, Berkshires 01238
    West Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
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    • Wi-Fi
    • Terrace
    • Central Heating
    • Outdoor Dining Area
    • Balcony
    • Patio
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    • Child-friendly
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    • Elder access
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    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
    Location Information
    West Stockbridge, Berkshires 12029
    1 / 7
    5 of 5 stars (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 stars 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 stars Reviewed 25 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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    Charlemont
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Mountain Views
    • Internet Access
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    • Grill
    • Central Heating
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
    Location Information
    Charlemont, Berkshires 01339
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    Becket
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Terrace
    • Balcony
    • Private Garden
    • Grill
    • Secure Parking
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    • Child-friendly
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    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating... View all property information
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    Becket, Berkshires 01223
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
    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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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    5 of 5 stars Reviewed 17 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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    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 | Quick View
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    • Porch
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    • Central Heating
    • Mountain Views
    • Grill
    • Skiing: Property Is...
    • Wi-Fi
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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 / 13
    4.5 of 5 stars (16) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Waterfront
    • Mountain Views
    • Hot Tub
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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 stars Reviewed 19 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 stars 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 / 15
    5 of 5 stars (2) Excellent
    Sandisfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    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
    Location Information
    Sandisfield, Berkshires 01255
    5 of 5 stars Reviewed 2 September 2015
    We had a great experience at this house. This house exceeded our expectations. It is bright and open with a big screened porch overlooking the woods and a beautiful garden. It...
    5 of 5 stars Reviewed 2 February 2015
    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
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    New Marlborough, Berkshires 01230
    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
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    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 / 10
    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...
    • Shared Outdoor Pool...
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
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    • x
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    • Elder access
    • ?
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    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 12 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 7 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 / 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
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    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
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed 21 February 2012
    I didn't want to leave. It was the most relaxing and tranquil time I could have imagined. The house is lovely and extremely comfortable -- clean, cozy and situated close to a...
    5 of 5 stars Reviewed 13 February 2012
    We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure...
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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 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 17 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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    Hinsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
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    • x
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    • Elder access
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    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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    Hinsdale, Berkshires 01235
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Stockbridge, Berkshires 01262
    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Porch
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    • Mountain Views
    • Satellite TV
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    see better & more photos of property here (copy-paste-edit in browser): tinyurl DOT com/hoqrp7n 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... View all property information
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    Lee, Berkshires 01238
    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
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
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    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
    Location Information
    Stockbridge, Berkshires 01260
    5 of 5 stars Reviewed 18 May 2010
    This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very...
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
    5 of 5 stars Reviewed 26 August 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Private Garden
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    • Pet-friendly
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    • x
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    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- KITCHENETTE W/ LG CEILING FAN,TV, DVD & 2 CLOSETS. ENTER DRESSING RM, LG BATH... View all property information
    Location Information
    Lenox, Berkshires 01240
    Williamstown
    4 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    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
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    West Stockbridge, Berkshires 01266
    Hancock
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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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    Hancock, Berkshires 01237
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 18
    5 of 5 stars (2) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home had 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 29 October 2015
    The Lake House was paradise. It is situated right in The Berkshires on Rte. 20 with easy access to everything. We golfed, canoed, played tennis, swam, hiked, went to museums...
    5 of 5 stars Reviewed 27 October 2015
    We were a group of 8 friends who have vacationed together annually. This was by far the best appointed house we have rented in 30 years. The owners, Margie and Frank were...
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    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Mountain Views
    • Grill
    • Satellite TV
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    • Central Heating
    • Hot Tub
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    • Pet-friendly
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    • Child-friendly
    • x
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    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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    Hancock, Berkshires 001237
    5 of 5 stars Reviewed 8 October 2010
    We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended...
    4 of 5 stars Reviewed 7 October 2010
    My husband and I stayed here with our 2 teen age girls last summer. We looked for a house that was close to Jiminy Peake for a family gathering. The house was well equipped and...
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Stockbridge, Berkshires 01262
    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    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 / 11
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
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    Great Barrington, Berkshires 01237
    4 of 5 stars Reviewed 10 September 2015
    I spent a delightful month at the Schoolhouse cottage. It's comfortably furnished, and while I was by myself most of the time it didn't feel crowded when friends or family stopped...
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    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
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    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    Pittsfield, Berkshires 01201
    3 of 5 stars Reviewed 18 August 2015
    The place was less than ideal in that the room smelled of smoke when we walked in. The bedroom had no windows and that felt very claustrophobic. It did have a kitchen which was...
    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Private Indoor Pool
    • Sauna
    • Mountain Views
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    • Pet-friendly
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    • x
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    About this property
    Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 23
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the... View all property information
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    Great Barrington, Berkshires 01230
    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
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    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Great Barrington, Berkshires 01230
    1 / 35
    5 of 5 stars (4) Excellent
    North Adams
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Mountain Views
    • DVD Player
    • Outdoor Dining Area
    • Parking
    • Terrace
    • Central Heating
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    • x
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    About this property
    Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the... View all property information
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    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 21 October 2015
    We chose the Rose and Goat Retreat for our annual girlfriends reunion. The lodge is spacious and accommodated all 8 of us. Beautiful views from every room in the house. Comfy...
    5 of 5 stars Reviewed 25 August 2014
    I booked the Rose & Goat Retreat for my sister's Bachelorette Weekend in the Berkshires! Not only was it the perfect location because it was only 11 miles away from our zip lining...
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    1 / 6
    5 of 5 stars (3) Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    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 1 week ago
    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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    Tyringham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Tyringham, Berkshires 01264
    1 / 16
    Becket
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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    Becket, Berkshires 01223
    1 / 17
    5 of 5 stars (2) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
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    • x
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    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars 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 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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    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    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...
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Child-friendly
    • x
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    • x
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    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake... View all property information
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    Lee, Berkshires 01238
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
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    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. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    Great Barrington, Berkshires 01230
    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Shared Indoor Pool
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    • Satellite TV
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 6 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 stars Reviewed 26 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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