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Sheffield Vacation Rentals

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    All 43 Rentals in Sheffield
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    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 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 15 kilometres of Sheffield.
    The Cottage at Great Falls1 / 18
    (20)Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Waterfront Cottage - 10 Mins to Great Barrington!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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    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 Garden
    • 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
    RiverSong Suite In The Berkshires1 / 52
    (15)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 June 22, 2019
    We were visiting friends in Great Barrington and found this wonderful place.It is right on a small river with lovely grounds. The hosts were very helpful.
    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...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Country Elegance in the Berkshires1 / 22
    (2)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 Garden
    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
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    North Egremont, Berkshires 01230
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    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 Garden
    • 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    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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    Amenities & Details
    • 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Garden
    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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    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 Garden
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Salisbury, CT
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Location Information
    Salisbury, Connecticut 06068
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Southfield
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Central Heating
    • Parking
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Location Information
    Southfield, Berkshires 01259
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
    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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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
    Great Barrington
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
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    Suitability
    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
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • 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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    Copake, New York 12529
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Great Barrington
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This updated home has a luxurious feel! Close proximity to downtown Great Barrington is convenient and allows for easy access to the world's cultural epicenter. Located on a dirt road in a gentle neighborhood. About 1/2 mile from Lake Mansfield. Dehon road cuts over to the lake! The upgraded...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Impeccable home and location. Recently upgraded, modern home provides a luxurious experience. Nestled above a lake on a quiet dirt road this home provides privacy and peace while only being minutes from downtown Great Barrington. Kitchen is equipped with stainless appliances and granite counter...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Salisbury, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires 01245
    Holiday Rental House - 2 Bathrooms, Sleeps 7
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires (ALL SEASONS): 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a very large heated swimming pool. The pool is...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    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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    • Private Garden
    • Porch
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    Pet friendly
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    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
    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a large heated swimming pool. The pool is completely...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When you pull into our long private driveway surrounded by nature, Our lovely cottage style home greets you with a rustic yet modern grey board and batten exterior and the sense of “coming home.” You then enter the home from a small wood deck that leads into the open concept kitchen/dining area....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Patio
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. For winter it is 15 minutes from Butternut family ski area (ideal for...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    New Marlborough
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    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
    Great Barrington
    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    About this property
    This charming former tavern and stage coach inn makes the perfect 4 season getaway for large group gatherings, family reunions, weddings or any occasion. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, skiing at Butternut Ski resort, and music and...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
    NEW! Lakefront Berkshires House w/Deck, Dock +Boat1 / 26
    (1)Average
    Housatonic
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My family liked the decor, had space to sleep with all our kids, and was close to great small towns in the Berkshires. The house was clean, had plenty of hot water and laundry...
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    About this property
    Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This 4-bedroom, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish,...
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    Housatonic, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Stay in a beautiful, stylish colonial house, built in 1800 and updated for maximum comfort. Open plan kitchen/living room with stunning cathedral ceilings, 5 bedrooms with views onto spacious, private 3-acre property and surrounding farmland. Fully equipped kitchen, washing machine, wood burning...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    New Marlborough
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental in New Marlborough. Nestled under the pine trees on the edge of Lake Buel, you'll have right-of-way access to the lake and unbeatable views of the picturesque landscape. Launch the 2 provided kayaks in...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Reconnect with Mother Nature at this 2-bedroom, 1-bath cabin loaded with character! Minutes from the Historic Mill River District, this vacation rental provides elements of the home like a well-equipped kitchen, views of the river, and warmth by the wood-burning stove. Listen to sounds of nature on...
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    New Marlborough, Berkshires 01244
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Terrace
    • Patio
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 150 feet of lakefront property on Lake Buel - a pristine 192-acre mountain lake - this lovely 3-bedroom, 2.5-bath home is sure to be the perfect 3-season getaway. Enjoy sitting on the deck to take in the water views, gathering around the fire pit to roast s’mores, or fishing right off the...
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    Monterey, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay a 5-minute walk from the Lake Garfield Beach and explore the area's historic attractions, outdoor recreation, and more at this 3-bedroom, 2.5-bath vacation rental! Up to 7 guests can enjoy a classic getaway at this country home, featuring a stone patio, gas grill, screened porch, and all the...
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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