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Holiday Rentals and Homes in Sheffield, MA

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    €469
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    1 / 35
    5 of 5 stars (16) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    €447
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    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 15
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    €335
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    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8
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    The following rentals are within 15 kilometers of Sheffield, Massachusetts.

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    1 / 11
    5 of 5 stars (15) Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (15) Make Enquiry
    Overview Reviews (15)
    Amenities & Details
    • Water Views
    • Deck
    • Stereo System
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed 29 May 2015
    My husband and I stayed here for a recent visit on a trip to New England. We chose this Falls Village cottage and it was truly wonderful. Everything from the location, right up...
    5 of 5 stars Reviewed 9 April 2015
    I have been traveling to the northwest of Connecticut since my teens, spending a lot of weekends at Lime Rock and Sharon where my daughters spent their summers in a camp. There...
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    €156
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    1 / 25
    5 of 5 stars (4) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Washer
    • Mountain Views
    • Central Heating
    • Deck
    • Fireplace
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed 7 July 2015
    I agree with all the previous reviews that this cabin met and exceeded the owner's representations, as well as our expectations. The house itself is extremely well designed and...
    5 of 5 stars Reviewed 1 July 2015
    My husband and I met friends for a long weekend in the Berkshires. This was an ideal location. The pictures are accurate and the house is even nicer in person. It met all our...
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    1 / 14
    5 of 5 stars (1) Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Deck
    • TV
    • Water Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 February 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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    €151
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    1 / 50
    5 of 5 stars (6) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
    Overview Reviews (6) Make Enquiry
    Overview Reviews (6)
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,... View all property information
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    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 9 July 2015
    This suite is located in a beautiful serene setting. Barbara keeps the suite very clean, and her attention to every detail is unmatched. We had a wonderful stay, and only wish...
    5 of 5 stars Reviewed 12 September 2014
    I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
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    €178
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    1 / 10
    5 of 5 stars (15) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3
    other travellers have booked this property
    Overview Reviews (15) Make Enquiry
    Overview Reviews (15)
    Amenities & Details
    • Boat Available
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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..... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 27 August 2015
    I stayed in the cottage with my girlfriend and our small dog and we had a fantastic time! The cottage had everything we needed (wifi, large bathroom, dining table, cable TV) and...
    5 of 5 stars Reviewed 26 August 2015
    My husband, 5 year old daughter and I had a great time at the Sigel's. The views are spectacular and we enjoyed being at the pool, going hiking and visiting the Rockwell museum in...
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    €313
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Deck
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed 5 January 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
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    €246
    / Night
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    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Water Park Nearby
    • Central Heating
    • Watersports Nearby
    • TV
    • DVD Player
    • Playground
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
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    Location Information
    Monterey, Berkshires 01245
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    €112
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    1 / 12
    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Alford, Massachusetts 01266
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    €156
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    1 / 15
    5 of 5 stars (4) Excellent
    Hillsdale, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Shared Indoor Pool
    • DVD Player
    • Water Views
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to the quiet confines of Copake Lake nestled in the heart of the Taconic Mountain Range in Columbia County, NY, bordering Massachusetts' Berkshire County. You wake up an hour past dawn, grab a cup of java and sit out on your private deck that overlooks shimmering Copake Lake, a 365 acre... View all property information
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    Location Information
    Hillsdale, New York 12529
    From
    €603
    / Night
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    €179
    / Night
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Linens Provided
    • Cooker
    • Refrigerator
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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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    Location Information
    Great Barrington, Berkshires 01237
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    €380
    / Night
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    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 13
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Water Views
    • Internet Access
    • Satellite TV
    • Stereo System
    • There Are Tennis...
    • Air Conditioning
    • DVD Player
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Hillsdale, New York 12529
    From
    €2,190
    / Week
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    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Deck
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    €168
    / Night
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    1 / 12
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Private Fishing...
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Mountain Views
    • Central Heating
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
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    €313
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    other travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Satellite TV
    • Stereo System
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 5 February 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
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    €170
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    1 / 15
    5 of 5 stars (7) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 9
    other travellers have booked this property
    Overview Reviews (7) Make Enquiry
    Overview Reviews (7)
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Deck
    • Stereo System
    • DVD Player
    • Private Fishing...
    • Fireplace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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,... View all property information
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    Location Information
    Copake, New York 12516
    4 of 5 stars Reviewed 11 August 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 area...
    5 of 5 stars Reviewed 5 September 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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    €4,023
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    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Playground
    • Internet Access
    • Mountain Views
    • Fireplace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Great Barrington, Berkshires 01230
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    €268
    / Night
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    1 / 19
    5 of 5 stars (3) Excellent
    Lakeville, CT
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Washer
    • Deck
    • Grill
    • Internet Access
    • Dryer
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Lakeville, Connecticut 06068
    5 of 5 stars Reviewed 27 May 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...
    5 of 5 stars Reviewed 6 May 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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    €156
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    4.5 of 5 stars (14) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other traveller has booked this property
    Overview Reviews (14) Make Enquiry
    Overview Reviews (14)
    Amenities & Details
    • Mountain Views
    • Playground
    • Water Views
    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • Air Conditioning
    Suitability
    • 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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    Location Information
    Monterey, Berkshires 01245 0933
    4 of 5 stars Reviewed 19 July 2015
    What a relaxing, quiet getaway! The cabin was rustic, roomy and secluded. Fully stocked with just about everything you could possibly need to enjoy your stay. We saw two bears...
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    €134
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    1 / 8
    Hillsdale, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Central Heating
    • Deck
    • Refrigerator
    • Fireplace
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Glorious views across meadows to distant mountains. Open-plan living/dining/kitchen with fireplace, and soaring ceiling. Many glass doors lead to decks where you may drink in the view. Great master bedroom suite with state of the art bathroom, two guest rooms, family room, media room and two guest... View all property information
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    Location Information
    Hillsdale, New York 12529
    From
    €201
    / Night
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    1 / 16
    5 of 5 stars (4) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7) BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS. 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 freshwater lake... View all property information
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    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 January 2015
    I'm sorry for not responding sooner. Your home was the best vacation rental in which I have stayed today and I rent frequently in the Berkshires. I am going to want to stay there...
    5 of 5 stars Reviewed 20 October 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 wowed...
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    €670
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    1 / 4
    4 of 5 stars (1) Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • Boat Available
    • Water Views
    • DVD Player
    • Stereo System
    • Central Heating
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Copake, New York 12529
    From
    €223
    / Night
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    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Washer
    • Mountain Views
    • Deck
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    €223
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Mountain Views
    • DVD Player
    • Stereo System
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
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    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed 20 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    €134
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    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Internet Access
    • TV
    • Waterfront
    • Mountain Views
    • Deck
    • Water Views
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 17 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
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    Salisbury, Connecticut 06079
    5 of 5 stars Reviewed 8 September 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 pace...
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    €416
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    1 / 33
    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveller has booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Game Room
    • Stereo System
    • Boat Available
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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    Great Barrington, Berkshires 01230
    From
    €1,520
    / Week
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    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Porch
    • Deck
    • DVD Player
    • Washer
    • TV
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    4 of 5 stars Reviewed 2 February 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    From
    €223
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    Great Barrington
    5 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Deck
    • Stereo System
    • Wi-Fi
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    €1,430
    / Week
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Grill
    • Dryer
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Refrigerator
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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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    Location Information
    New Marlborough, Berkshires 01230
    From
    €335
    / Night
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    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Watersports Nearby
    • TV
    • DVD Player
    • There Are Tennis...
    • Deck
    • Air Conditioning
    • Wi-Fi
    • Horse Riding Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
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    North Egremont, Berkshires 01230
    From
    €648
    / Night
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    Hillsdale, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 14
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
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    Location Information
    Hillsdale, New York 12529
    From
    €156
    / Night
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    Hillsdale, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Horse Riding Nearby
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Hillsdale, New York 12529
    From
    €447
    / Night
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    Great Barrington
    3 Bedrooms, 8 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Ping Pong Table
    • Game Room
    • Satellite TV
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    SummerStone is an elegant country home beside a state forest the NYT once referred to as 'the best kept secret in the Berkshires'. Enjoy red oak floors, tumbled marble showers, cozy fireplaces and soaring ceilings. Go kayaking, biking, swimming or hiking then relax on the 600 sq. ft. porch. Ping... View all property information
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    Location Information
    Great Barrington, Berkshires 01258
    From
    €1,073
    / Week
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    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Patio
    • Dryer
    • TV
    • Washer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    €206
    / Night
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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Linens Provided
    • Cooker
    • Fireplace
    • Mountain Views
    • Wi-Fi
    • Deck
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    €1,117
    / Week
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
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    Location Information
    Monterey, Berkshires 01245
    From
    €156
    / Night
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    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Stereo System
    • Central Heating
    • Washer
    • Grill
    • Deck
    • Wi-Fi
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Copake Falls, New York 12517
    From
    €179
    / Night
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    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Patio
    • Grill
    • Game Room
    • Dryer
    • Housekeeping...
    • Mountain Views
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to... View all property information
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    Location Information
    Copake, New York 12516
    From
    €115
    / Night
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    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Grill
    • Linens Provided
    • Mountain Views
    • Central Heating
    • Watersports Nearby
    • Balcony
    • Horse Riding Nearby
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Copake, New York 12516
    From
    €128
    / Night
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    1 / 6
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Grill
    • Water Views
    • Refrigerator
    • Dryer
    • DVD Player
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
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    Location Information
    Copake, New York 12529
    From
    €319
    / Night
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    1 / 23
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Hot Tub
    • Satellite TV
    • Deck
    • Air Conditioning
    • Internet Access
    • Fireplace
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Great Barrington, Berkshires 01230
    From
    €128
    / Night
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    1 / 6
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Deck
    • Refrigerator
    • Grill
    • Washer
    • Water Views
    • Air Conditioning
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
    Make Enquiry
    Location Information
    Copake, New York 12529
    From
    €179
    / Night
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    1 / 9
    Copake, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 17
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Internet Access
    • Washer
    • Boat Available
    • DVD Player
    • Central Heating
    • Satellite TV
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
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    Location Information
    Copake, New York 12516
    From
    €319
    / Night
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    1 / 23
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Fireplace
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Stereo System
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    Location Information
    Great Barrington, Berkshires 01230
    From
    €179
    / Night
    View Details
    1 / 9
    Copake, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 17
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Boat Available
    • Stereo System
    • Waterfront
    • Central Heating
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
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    Location Information
    Copake, New York 12516