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Sheffield Vacation Rentals

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    Don't let other travelers get your favorite Sheffield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 37 Rentals in Sheffield
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    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Apple Cottage1 / 10
    (4)Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 10 miles of Sheffield.
    The Cottage at Great Falls1 / 18
    (19)Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Mountain Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 15, 2017
    Danielle responded to my vacation request in record time, and was very attentive before, during and after our stay. Everything was perfect when we arrived - the cottage was...
    Reviewed September 14, 2016
    Enjoyed our stay at this beautiful, well appointed cottage and would book again.Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
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    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful...
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    Location Information
    Falls Village, Connecticut 06031
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    North Egremont
    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 August 19, 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 November 2, 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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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (2)Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Outdoor Dining Area
    • Central Heating
    • Wi-Fi
    • Private Yard
    • Grill
    • DVD Player
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 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 February 6, 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
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    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Yard
    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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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    Great Barrington
    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 August 13, 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 August 3, 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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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (20)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 20, 2017
    Karl and his place are supremely magical. The cottage is nestled in the woods on activated lands with a beautiful comforting peaceful lake, nature trails, less than an hour from...
    Reviewed September 21, 2017
    We rented Karl's house for a 10-day time frame, to enjoy some family vacation time with our children and grandchildren. I have really struggled with what to say about this...
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    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. **The house has a Jacuzzi and ROKU access to online (cable) TV. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice...
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    Monterey, Berkshires 01245 0933
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Country Elegance in the Berkshires1 / 22
    (1)Excellent
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 30, 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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    Location Information
    Great Barrington, Berkshires 01236
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Waterfront Lake Buel Cottage - Open Year-Round!1 / 24
    (4)Excellent
    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Waterfront
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 30, 2018
    We had an excellent time with our two kids (7 and 8). The house is right on the lake with a great deck and amazing views. We used the kayaks every day. Location was great...
    Reviewed June 22, 2018
    Perfect location, perfect weather, beautiful view! Excellent owner, Carol, who responded to all our questions immediately. Would go back again in a minute.
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never...
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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Riverwood - Cozy Carriage House in the Woods1 / 11
    (1)Excellent
    Falls Village, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2018
    I would rate this higher than 5 stars. The location was perfect for our week. Close to family in the area, hiking, kayaking and motorcycling. The carriage house is immaculate...
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    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area....
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    Location Information
    Falls Village, Connecticut 06031
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming 2+2 Lakeside Cottage on Best Lake in CT1 / 37
    (1)Excellent
    Salisbury, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our...
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    About this property
    For the price of a motel room, enjoy a cottage on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 NIGHT STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. MONTHLY RATE REQUIRES 32 NIGHT MINIMUM STAY....
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    Location Information
    Salisbury, Connecticut 06079
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 17
    (8)Excellent
    Copake, NY
    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 August 10, 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the...
    Reviewed September 5, 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
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    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,...
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    Location Information
    Copake, New York 12516
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Renovated Barn1 / 15
    (1)Excellent
    Taconic, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2018
    Bebe (the owner) was extremely communicative from beginning to end. The house was even more beautiful in person. We will definitely be booking here again!
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    About this property
    Charming renovated Barn, very private, with pastoral views. Recently renovated throughout, the house features a double-height, vaulted ceiling in the Kitchen, Dining, and Living Rooms, with great light and views. Open deck off the Living Room overlooking a large, private meadow. Within a...
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    Location Information
    Taconic, Connecticut 06068
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Smith Farm Homestead1 / 12
    (6)Excellent
    Alford
    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 October 1, 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 February 4, 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
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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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    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore...
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    Location Information
    Copake Falls, New York 12517
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington
    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 March 15, 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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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
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    Location Information
    Alford, Berkshires 01266
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The...
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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 2 Bathrooms, Sleeps 7
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    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
    • Mountain Views
    Suitability
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    Great Barrington
    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 November 16, 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed November 16, 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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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    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Salisbury, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    East Twin Lakes, a charming three-bedroom lakefront cottage with private two docks, 200 feet of shore front with gorgeous views. The lake is clean and has the best fishing in Connecticut. Enjoy boating, water skiing, canoeing, sailing or fishing. The cottage is furnished and has a window air...
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    Salisbury, Connecticut 06068
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Marlborough
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    The guest suite is within 'Keyes House,' a quintessential 19th century Greek Revival colonial. It is conveniently located in a small, bucolic village in Southern Berkshire County that is on the National Register of Historic Districts. The entire home, including the two-room suite, has been...
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    New Marlborough, Berkshires 01230
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
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    • Grill
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the...
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    Copake, New York 12529
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Great Barrington
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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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    Great Barrington, Berkshires 01230
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Porch
    • Outdoor Dining Area
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Monterey
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Mountain Views
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Monthly discount for stays of 30 nights or more Jan-April 2018* 'Smiling Dog Meadow' offers the ideal escape to Massachusetts's scenic Berkshires region! Nestled on 5 acres, this newly renovated home for up to 12 guests features 4 bedrooms, 2.5 baths, and a waterfront location with access to a...
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    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Great Barrington
    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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    Great Barrington, Berkshires 01230
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    North Egremont
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
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    • 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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    New Marlborough
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental cottage in New Marlborough that sleeps 2. Nestled under the pine trees on the edge of Lake Buel, you'll have unbeatable views of the picturesque landscape, framed by the large windows throughout the...
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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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