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Hillsdale Holiday Homes

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    Don't let other travellers get your favourite Hillsdale area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 46 Rentals in Hillsdale
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    Beautifully decorated & immaculate log chalet1 / 26
    (16)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hillhouse Log Cabin1 / 18
    (1)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Overnight at Althouse -Higgins1 / 11
    (3)Excellent
    Hillsdale
    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 3 January 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 4 November 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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    Hillsdale, New York 12529
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 15 kilometres of Hillsdale.
    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
    Reviewed 3 November 2017
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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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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    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed 6 June 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 28 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a haven, a state...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Berkshire Barn Paradise1 / 23
    (1)Excellent
    Craryville
    2 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Grill
    • Hot Tub
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    The pictures and description don't do this place justice! There are no details left undone - Joe, our host, has thought of everything. The home was beautiful and FULLY stocked...
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    About this property
    You won't see another property like this. This is no ordinary barn. As you step inside you are greeted by a custom made dining room table that comfortably sits 16-20 people! Sit back and watch the deer/turkey/pheasant go by your window. Experience full upscale luxury in a beautifully restored and...
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    Craryville, New York 12529
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 8
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    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    North Egremont, Berkshires 01230
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 17
    (8)Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Country Elegance in the Berkshires1 / 22
    (1)Excellent
    Great Barrington, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2018
    We rented this house for our family coming together in celebration of my Brice getting married.mu sister showed up to the Home first but she was sure she was at the wrong place...
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    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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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    First of all, the area where this house is is AMAZING. My husband and I have been coming to the Berkshires for years but we had never driven in this particular neighborhood. The...
    Reviewed 3 August 2018
    The picture is real (except we didn't see the rainbow). It's a lovely first floor studio cottage with a kitchenette; very comfortable, well stocked, and beautifully decorated...
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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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    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed 14 November 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
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    Location Information
    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (2)Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Central Heating
    • Wi-Fi
    • Private Garden
    • Grill
    • DVD Player
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    I just spent three nights enjoying Ilana’s house on Robinson Pond.Fishing and swimming in the lake.Eating and enjoying cocktails on her beautiful deck.Everything was really nice...
    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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    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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    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
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    Austerlitz, New York 12017
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
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    Ghent, New York 12075
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    Location Information
    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
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    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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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    Location Information
    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    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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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Copake Falls
    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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    Copake Falls, New York 12517
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Craryville
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1860s FARMHOUSE WITH CHARM AND MODERN UPDATES. COME SPEND THE WINTER IN THE COUNTRY! CLOSE TO GREAT DINING, SHOPPING AND SKIING. Ask about our discounts for multi-week and monthly stays! Business ready: self check-in, wireless internet, wireless printing An Idyllic Country Escape 2 Hours from...
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    Craryville, New York 12521
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Shared Garden
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes...
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    Location Information
    Austerlitz, New York 12017
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 17 November 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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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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    Location Information
    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Smith Farm Homestead1 / 12
    (6)Excellent
    Alford, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2018
    This was a perfect place for a bit of R & R. Friendly owners and luxurious room that was clean and comfortable. The home has a historical atmosphere in a beautiful country...
    Reviewed 4 February 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!
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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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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 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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    Location Information
    Alford, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
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    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas. The bedroom and living...
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    Location Information
    Ghent, New York 12075
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Terrace
    • Washer
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    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...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
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    Pet friendly
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    About this property
    Located in the center of Columbia County, NY this retreat is a great spring board to all it has to offer: minutes to Hudson, Chatham, High Falls, hiking trails, farms, streams. You’ll love the varied bright cozy rooms to lounge in, including a screened front porch. Most relaxing is to hang out on...
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    Location Information
    Philmont, New York 12534
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Craryville
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note the homeowner lives on site, in a completely separate home with some shared outdoor amenities* Live the lake life at this waterfront cottage in New York! The 1-bedroom, 1-bath Craryville vacation rental home sleeps up to 4 guests and provides visitors with the opportunity to utilize...
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    Craryville, New York 12521 5019
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Central Heating
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    • Balcony
    • Housekeeping Included
    • Grill
    Suitability
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Great Barrington, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 2016 Smithsonian Magazine deemed Great Barrington, 'The Best Small Town in America.' Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
    • DVD Player
    • Washer
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    • Central Heating
    • Cable/satellite TV
    • 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Great Barrington, MA
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • 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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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    Craryville
    3 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Balcony
    • Terrace
    • DVD Player
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely refurbished 1827 post and beam Barn renovated July 2012 featuring an Adirondack 'chic' style. Appointed with Mitchell Gold furniture, a custom built 6' round dining room table, indoor fireplace (Dec 2013), double insulated windows, concrete counter-tops and island/bar, stainless...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 14
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    Craryville
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    • Terrace
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    • DVD Player
    • Central Heating
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 2
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    Craryville
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Terrace
    • Central Heating
    • Patio
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Private Garden
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    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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    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    West Stockbridge, Berkshires 01266
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    NEW! 'Butterfly Hill' 2BR West Stockbridge House1 / 24
    (1)Excellent
    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • DVD Player
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    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We thoroughly enjoyed our week at Butterfly Hill. It was near Tanglewood, our main reason for the visit, and all the nearby towns where we found good restaurants and shops. We...
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    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    North Egremont, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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    North Egremont, Berkshires 01258
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Craryville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
    • Balcony
    • DVD Player
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Craryville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • DVD Player
    • Central Heating
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Craryville
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping...
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    Location Information
    Spencertown, New York 12165
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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