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Sheffield Pet Friendly 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.
    8 Matching Rentals in the Sheffield AreaView all 33 rentals
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    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 miles 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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    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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    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
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 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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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 Yard
    • 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
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Barrington
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • 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
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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