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Sheffield House Rentals

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    Don't let other travellers get your favourite Sheffield area holiday rental. You're so close to securing your perfect getaway. Book today.
    19 Matching Rentals in the Sheffield AreaView all 32 rentals
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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.
    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (20)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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
    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 16 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
    01236, Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    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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    Location Information
    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    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 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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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Amenities & Details
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 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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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 5 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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    Amenities & Details
    • 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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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Amenities & Details
    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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
    01236, Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Renovated Barn1 / 15
    (1)Excellent
    Taconic, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 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
    06068, Taconic, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
    01245, Monterey, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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
    01230, Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    01230, New Marlborough, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    12529, Copake, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Suitability
    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
    01245, Monterey, Berkshires
    Holiday Rental House - 2 Bathrooms, Sleeps 7
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    01245, Monterey, Berkshires
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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