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  • Mountaintop Cabin w/Waterfront & Amazing View

    Bennington, Vermont

    This mountain top chalet is the perfect vacation home for outdoor enthusiasts, families, or those just looking for a quiet, relaxing escape. Beautiful and serene sitting on a small lake at 2,300... ...more

    Beds: 2 Baths: 2 Property type: Chalet (6) Very Good
    $175 / Nightly
  • Karin's Place

    Bennington, Vermont

    There is something for everyone at Karin’s Place–from the peaceful and tranquil gardens, gazebo and pool while the kids play on the pirate ship to a full-size movie screen with surround sound and... ...more

    Beds: 7 Baths: 6 Property type: House (0)
    $1,350 / Nightly
  • Country Estate: Main Lodge - 4 Bdrms, 3.5 bath

    Bennington, VT

    Located at the end of a winding country road and nestled against the base of Mount Anthony, the property has 350+ private acres to hike or walk, two lovely ponds for swimming, stunning views of... ...more

    Beds: 4 Baths: 4 Property type: House (51)
    $511 / Nightly
  • Historic Home in Old Bennington, Vermont

    Bennington, VT

    This lovely family home was built in 1828. The home is furnished with fine antiques. Located on over two acres of gardens, lawns and meadow, the house is just down the street from the historic... ...more

    Beds: 3 Baths: 3 Property type: House (32)
    $282 / Nightly
  • Victorian Home in Bennington, Vermont

    Bennington, VT

    This home was originally built in the mid-1800's. It has been completely remodeled to preserve the historic beauty of the home. Modern conveniences were added. The house is located two blocks off... ...more

    Beds: 3 Baths: 3 Property type: House (19)
    $459 / Nightly
  • Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!

    Bennington, VT

    Whether you're coming to Bennington for the fall colors, winter sports, spring graduations, summer street festivals and parades, or college campus visits, this studio apartment will provide a... ...more

    Beds: 0 Baths: 1 Property type: Studio (6) Very Good
    $168 / Nightly
  • 1920's Bennington Vermont Guest Barn

    Bennington, VT

    Very comfortable accomodations with just about everything brand new down to quality mattresses and bedding. New kitchen appliances and compliments along with bottled spring water in the fridge.... ...more

    Beds: 3 Baths: 1 Property type: Barn (8) Wonderful
    $163 / Nightly
  • The Old Academy, stay in a part of history.

    Bennington, VT

    Located along the beautifully tree-lined historic Monument Avenue, in the village of Old Bennington, The Old Academy stands proudly. While the residence itself dates back to 1821, it was renovated... ...more

    Beds: 4 Baths: 3 Property type: House (6) Wonderful
    $386 / Nightly
  • Bennington Guest Farmhouse

    Bennington, VT

    Large Gracious Victorian Farmhouse lovingly restored to accommodate nine guests in a quaint relaxed atmosphere. Conveniently located: 1 mile to Bennington College, and a short distance to... ...more

    Beds: 5 Baths: 2 Property type: House (2) Exceptional
    $208 / Nightly
  • Secluded Luxury In The Country, Close To Culture

    Bennington, VT

    There is something for everyone at Karin’s Place–from the peaceful and tranquil gardens, gazebo and pool while the kids play on the pirate ship to a full-size movie screen with surround sound and... ...more

    Beds: 9 Baths: 6 Property type: Estate (25) Exceptional
    $1,580 / Nightly

Bennington: Vacation Rental By Owner

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Bennington. Many accommodations in Bennington provide "Golf", there are 8, or there are 7 of Vacation Rentals in Bennington with a "Hiking", there are also 7 with "Non Smoking Only", which is another great reason to visit Bennington.