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North Bennington Holiday Homes

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    Don't let other travellers get your favourite North Bennington area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in North Bennington
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    North Bennington
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of North Bennington.
    Sunderland, VT
    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Petersburg, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Williamstown, MA
    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    • Patio
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lots of space, great yard, walk to everything: restaurants, museums, Williams College, theater, night life, etc. Plus, nearby ski and tubing areas. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally...
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    Location Information
    Williamstown, Berkshires 01267
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
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    Williamstown, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Shared Indoor Pool
    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thanksgiving week Berkshire Luxury condo/4 1Bedroom, 1Bath, Living Room with fireplace & Kitchen Available November 20-27 Thanksgiving week Between Mt. Greylock, Pittsfield, Great Barrington, Stockbridge, Krupalu, Tanglewood, Jacob's Pillow, The Mount, NOrman Rockwell Museum, Daniel Chester French...
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    Williamstown, Berkshires 01267
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy Lakefront Cottage1 / 13
    (1)Excellent
    Somerset, VT
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 January 2016
    Yes, it's worth staying at this charming cabin on the lake for the views even in chiller times. We enjoyed a holiday time bedding 6 in their rooms. An easy to use kitchen with...
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    About this property
    Cozy Woodford Lakefront Cottage is perfect vacation spot for families and outdoor enthusiasts or those seeking relaxing get away. The cottage sits high overlooking Woodford Lake with a spectacular view of Vermont’s beautiful mountain range. Woodford is the highest evaluated town in all of the...
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    Somerset, Vermont 06076
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Green Mountain Retreat1 / 18
    (1)Very good
    Sunderland, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This house was quiet, well equipped, perfectly uncluttered, clean and warm. The kitchen window Roaring Branch River was stellar. The exterior is unassuming and deceptive; the...
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    About this property
    This is a modern three bedroom, two bath in one of the most beautiful places in New England - nestled in the Green Mountain National Forest, across the road from the Roaring Branch River. About 12 minutes from Manchester and 20 minutes from Bennington. It is close to all of the best trails in...
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    Sunderland, Green Mountains 05262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cambridge, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful full-house on the edge of 1000 acres of wetland and wildlife. 30 minutes from Saratoga Springs. Perfect for families, groups, and events that want to be in nature, with all of the comforts of modern living. Enjoy 3 rooms, living room, kitchen, and cozy fireplace. See pictures to find all...
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    Cambridge, New York 12816
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Williamstown, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Central Heating
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Washer
    • Private Garden
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have been renting our Williamstown home to vacation guests for 9 years, and we are also open to long-term academic rentals. This charming 1890s farmhouse is located on a quiet, lightly-traveled street 3 blocks west of the Williams College campus. It is well-maintained and sleeps 5 upstairs, in 2...
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    Williamstown, Berkshires 01267
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Shaftsbury, VT
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadowood Farm is located in the Green Mountains and between Bennington and Manchester, Vermont. Designer discount shopping, art galleries, antique stores, country stores, and museums are abundant. There are five covered bridges in the immediate area. Bennington College is four miles from the...
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    Location Information
    Shaftsbury, Green Mountains 05262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    Cambridge, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This small study offers a peaceful view of the forest and mountains. It's designed as a classy yet cozy room. Access the entire house, lounge area, and kitchen during your stay. Locally you'll find hiking trails, cute towns, wildlife, horse riding ranches, white water rafting, and more. The entire...
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    Cambridge, New York 12816
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cambridge, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sit above the entire property in a beautiful loft with mountain and country views. Windows surround the entire second-floor room. Access the entire house, lounge area, and kitchen during your stay. Locally you'll find hiking trails, cute towns, wildlife, horse riding ranches, white water rafting,...
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    Cambridge, New York 12816
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Petersburg, NY
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Terrace
    • Balcony
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home to the 'Fox Hollow Music Festival' from 1968 - 1980, The Lodge is rich in history & beauty. Built in 1970 and named 'The Lodge', it was used as a rehearsal space by Festival musicians, and its magnificent parquet floor hosted many dance performances. It was originally one, gigantic, open...
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    Petersburg, New York 12138
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Cambridge, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This corner room boasts giant windows with plenty of natural light. It's tucked peacefully away from the main house. Access the entire house, lounge area, and kitchen during your stay. Locally you'll find hiking trails, cute towns, wildlife, horse riding ranches, white water rafting, and more. The...
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    Location Information
    Cambridge, New York 12816
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cambridge, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this private Cambridge log cabin nestled in a grove of woods. With updates and remodels throughout, this private vacation rental home is warm and inviting. The 3 bedrooms, 2 bathrooms, and additional sleeping areas in the enclosed porch and living room provide comfortable space for up to...
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    Location Information
    Cambridge, New York 12816
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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