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Sheffield Vacation Rentals

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    All 52 Rentals in Sheffield
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    Sheffield
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Apple Cottage1 / 10
    (4)Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 28, 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
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    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the...
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    Sheffield, Berkshires 01257
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sheffield
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Sheffield, Berkshires 01257
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Washer
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    Pet friendly
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    Sheffield, Berkshires 01257
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant 1500sf  Apartment For Sophisticated Travelers In Southern Berkshires1 / 23
    (1)Excellent
    Sheffield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    • Patio
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Sheffield, Berkshires 01257
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Elterwater--Sought after and rare private idyllic Berkshire lakefront1 / 23
    (20)Excellent
    Sheffield
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    Pet friendly
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    Smoking allowed
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    Sheffield, Berkshires 01257
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful Berkshire Home W Tennis Court; Close to Skiing!1 / 24
    (14)Excellent
    Sheffield
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Internet Access
    • Satellite TV
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Sheffield, Berkshires 01257
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    Renovated Farmhouse with Terrific Views, Fire pit, and Teepee1 / 24
    (2)Excellent
    Sheffield
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Sheffield, Berkshires 01257
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Gorgeous Sheffield Home in Heart of Berkshires1 / 23
    (13)Excellent
    Sheffield
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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    Location Information
    Sheffield, Berkshires 01257
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    The following rentals are within 10 miles of Sheffield.
    Charming 2+2 Lakeside Cottage on Best Lake in CT1 / 37
    (1)Excellent
    Salisbury, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our...
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    About this property
    For the price of a motel room, enjoy a cottage on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 NIGHT STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. MONTHLY RATE REQUIRES 32 NIGHT MINIMUM STAY....
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    Salisbury, Connecticut 06079
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (2)Average
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2017
    Ray was very quick to respond to all our rental questions. We had a wonderful weekend at this home. It was very clean and welcoming to our party of 6 . The kitchen was fully...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lakeville, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Yard
    • Mountain Views
    • Parking
    • Wi-Fi
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    -Salisbury School -Hotchkiss -Indian Mountain School -Lime Rock Park Race Track Just steps to everything in town! Or grab a tall glass of Lemonade and a good book & relax on the porch. This petite in-town home is convenient to restaurants, shops, & Lake. The perfect spot to getaway & enjoy...
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    Location Information
    Lakeville, Connecticut 06039
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (18)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    We rented Karl's house for a 10-day time frame, to enjoy some family vacation time with our children and grandchildren. I have really struggled with what to say about this...
    Reviewed November 18, 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...
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    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. **The house has a Jacuzzi and ROKU access to online (cable) TV. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice...
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    Monterey, Berkshires 01245 0933
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautifully decorated & immaculate log chalet1 / 26
    (14)Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Mountain Views
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2017
    Beautiful log cabin on a quiet street, surrounded by "peace and quiet". Loved the accommodations - easily sleeps 6 with two full baths. Kitchen has all the...
    Reviewed November 28, 2016
    The cabin was exactly what we were expecting from the pictures shown on TripAdvisor. It was beautiful, clean, comfortable, and cozy. There were 5 adults in our group, but the...
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    About this property
    3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two...
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    Location Information
    Hillsdale, New York 12529
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Copake Lakeview Ranch1 / 26
    (2)Excellent
    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Parking
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2016
    Fantastic place to unwind and reconnect with nature: huge oak trees frame the view of the lake & mountains in the distance. Birds, wind, and occasional fish splashing in...
    Reviewed October 31, 2015
    We were delighted to find this attractive cottage on Robinson Pond. We enjoyed watching the ducks and geese out the expansive windows and were so pleased to see no other humans...
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    About this property
    Elegant and tranquil 2 level lakefront retreat, the perfect escape for any season. 3 bedrooms, 2 bath plus a powder room, gourmet kitchen with island counter, cathedral ceilings, large deck facing lake and spectacular Taconic mountain range + small screened porch. Breathtaking lake and mountain...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Lakefront 2BR New Marlborough Cottage w/Deck1 / 24
    (1)Excellent
    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Mountain Views
    • Parking
    • DVD Player
    • Central Heating
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this serene lake-front Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this property is sure to give you an experience in the Berkshires that you will never forget! THE PROPERTY...
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    New Marlborough, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Berkshires: Romantic Cottage with spectacular view1 / 13
    (22)Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We loved visiting the Berkshires, and the cottage was a perfect romantic heart of our vacation. The scenic views right from the cottage, the pool a few steps away, and great...
    Reviewed August 5, 2016
    What a charming, relaxing, and peaceful rental in the very heart of Berkshires cultural activities and venues. The view and pool are splendid, the apartment itself is private...
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.....
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 15
    (8)Excellent
    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the...
    Reviewed September 5, 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
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    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore...
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    Location Information
    Copake Falls, New York 12517
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedroom Furnished House in Lakeville Connecticut1 / 42
    (3)Excellent
    Lakeville, CT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Porch
    • Washer
    • Satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2014
    My friends and I stayed at this house for a race weekend at Lime Rock Park. The location of this house is perfect - 15 minutes from the track, walking distance from a small lake...
    Reviewed May 6, 2014
    We rented this sweet home in Lakeville for the bride and bridesmaids for my son's wedding. The bridal party came from far and wide and this was the perfect destination for the...
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    About this property
    This newly renovated 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. This house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove which offers many recreational...
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    Location Information
    Lakeville, Connecticut 06068
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Smith Farm Homestead1 / 12
    (5)Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 4, 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
    Reviewed October 16, 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked...
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural...
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    Location Information
    Alford, Berkshires 01266
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Riverwood - Cozy Carriage House in the Woods1 / 11
    (1)Excellent
    Falls Village, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Parking
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 2016
    I only wish my mobility was better to take a walk on this beautiful property very close to Lime Rock Park and many other cultural attractions. Owners were very nice and...
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    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area....
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    Falls Village, Connecticut 06031
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Taconic, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming renovated Barn, very private, with pastoral views. Recently renovated throughout, the house features a double-height, vaulted ceiling in the Kitchen, Dining, and Living Rooms, with great light and views. Open deck off the Living Room overlooking a large, private meadow. Within a...
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    Location Information
    Taconic, Connecticut 06068
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Overnight at Althouse -Higgins1 / 11
    (3)Excellent
    Hillsdale, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 2017
    Great, clean property. Plenty of space and privacy for a family of 4. Kitchen and apt. well stocked (linens, towels, etc). Everything you need from a store is within 1,000 feet...
    Reviewed November 4, 2015
    C'était tellement bien, que j'ai déjà envie d'y retourner!!As a French citizen, I can affirm that my stay at Lynne and Bill's loft was perfect! No noise, comfortable and with...
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    About this property
    We found a great circa 1845 house in the Berkshire/Taconic Mtn area and fully renovated the entire building creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Fully equipped efficiency kitchen with a W/D, marble bath, sleeps 6...
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    Location Information
    Hillsdale, New York 12529
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (3)Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Parking
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discounted monthly rentals during ski season (January and February) at $3,499/month and weekly in March at $899/week. This house has been extensively renovated. The chef's kitchen and living room were combined for a large open family area. The kitchen was completely renovated with high end wood...
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    Location Information
    Copake, New York 12521
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Hillsdale, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms...
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    Hillsdale, New York 12529
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Hillhouse Log Cabin1 / 18
    (1)Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Cozy modern log cabin nestled in the Berkshires in a large wooded area with landscaped yard on a small river. The cabin has a full service kitchen and a great room with dining and lounging space. There is a full entertainment center with furnished recorded music and movies. Bedrooms and bath are...
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    Hillsdale, New York 12529
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 13
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
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    • Mountain Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 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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    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,...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the splendor of the Berkshires from this 3-bedroom, 2-bathroom vacation rental house which sleeps 8 in Great Barrington. Situated on a 3-acre lot overlooking the Housatonic River, this home provides an idyllic setting for your retreat. Not only can you relax in the tranquility of your...
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    Great Barrington, Berkshires 01230
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (1)Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 6, 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
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    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    : Close to downtown : Just a short distances to Tanglewood , Butternut : Ski Resort. Spas. Hiking and many wonderful : Restuaunts : House is located in country setting cozy and spacious. Ski resorts close. Great fall get getaway apple orchard within 10 mins. Breath taking fall colors . The space...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires 01245
    Rental Home - 2 Bathrooms, Sleeps 7
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    Cozy and clean in Gt Barrington- 1 week in summer!1 / 10
    (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
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lake House in the Berkshires1 / 19
    (1)Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 12, 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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    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...
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    Location Information
    North Egremont, Berkshires 01230
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
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    Alford, Berkshires 01266
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,...
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    Location Information
    Great Barrington, Berkshires 01236
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Mountain Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Great Barrington, Berkshires
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The Cottage at Great Falls1 / 11
    (18)Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    • Mountain Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2016
    Enjoyed our stay at this beautiful, well appointed cottage and would book again.Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
    Reviewed September 3, 2016
    We spent a very relaxing weekend here and took great advantage of the deck overlooking the river. Everything was as described and depicted in photos. It was awesome to hear...
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    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful...
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    Location Information
    Falls Village, Connecticut 06031
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    TAKE ME HOME, COUNTRY ROADS1 / 16
    (4)Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed October 20, 2014
    We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really...
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    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7)<BR><BR>BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS.<BR><BR>This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the...
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    Location Information
    Copake, New York 12529
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    RiverSong Suite In The Berkshires1 / 52
    (12)Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Beautiful place, lovely accomodations, wonderful landscape abounds, and very nice and warm hosts. Very comfortable, spacious and private.
    Reviewed March 14, 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Great Barrington
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Great Barrington, Berkshires 01230
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Central Heating
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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