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Latest Vacation Rentals in Bennington County, VT

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Arlington (30)

3 Br Private Vacation Home Vacation Rental In Sunderland, Vermont

Welcome to The Skyline Cabin! A one-of-kind, modern Vermont escape central to dining, shopping, and culture. Overlooking several mountain ranges, this high-end getaway offers an unparalleled luxury...

Created on Jun 16, 2024
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Bennington (37)

3 Br Apartment Vacation Rental In Bennington, Vermont

Welcome to the Cozy Getaway, a newly renovated 3-bedroom condo on Branch Street in beautiful Bennington, Vermont. This charming and comfortable home is perfect for small families or business...

Created on Jun 16, 2024
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Bondville (179)

4 Br Private Vacation Home Vacation Rental In Winhall, Vermont

Sleeps 8 plus. Newly renovated with 2 MASTER SUITES on the main floor and 2 other bedrooms with 2 beds each upstairs. Perfect for 2 families or a group of friends. Minutes to Stratton by Shuttle...

Created on Jun 16, 2024
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Dorset (39)

1 Br Apartment Vacation Rental In Dorset, Vermont

Close to Beautiful Manchester Center, Vermont.The apartment is located on 33 private acres next to a babbling brook that spills into the nearby Metawee River. Located in exclusive Dorset Hollow and...

Created on Jun 16, 2024
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East Dorset (19)

4 Br Private Vacation Home Vacation Rental In East Dorset, Vermont

Our house is beautifully situated on 3 acres, top of a hill in a clearing. Large covered porch faces east across a meadow towards the Green Mountain National Forest and the notch carved by the Mad...

Created on Jun 16, 2024
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Manchester (38)

6 Br Private Vacation Home Vacation Rental In Manchester, Vermont

Bask in the best views in Vermont from the Equinox Views Villa, a private 6 bedroom/6 bathroom home located on the 30-acre resort Wilburton Resort in Manchester Village, Vermont. This beautifully...

Created on Jun 16, 2024
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Manchester Center (130)

5 Br Private Vacation Home Vacation Rental In Manchester, Vermont

Swiss-style 5BR/5BA 5200 sq ft enchanting villa in the heart of Manchester on 4 stunning acres. Accommodates 15-20 guests with a ground-level bedroom and full bath. The villa offers a billiards...

Created on Jun 16, 2024
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North Bennington (5)

1 Br Private Vacation Home Vacation Rental In North Bennington, Vermont

This cozy 1 bedroom cottage unit is located on a casual farm. Get a little taste of Vermont Country Living . Chickens, turkeys and ducks are free range here. Feel free to pet the Dutch rabbits....

Created on Jun 16, 2024
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North Pownal (2)

5 Br Private Vacation Home Vacation Rental In Pownal, Vermont

Find connection in this scenic mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD &/or...

Created on Jun 16, 2024
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Peru (70)

3 Br Condo Vacation Rental In Peru, Vermont

Breathe in the crisp, clean air of Vermont at this 3-bedroom, 2-bath vacation rental at Bromley Mountain Ski Resort! Spend your days in the community saltwater pool, getting competitive on the clay...

Created on Jun 16, 2024
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Pownal (12)

4 Br Private Vacation Home Vacation Rental In Pownal, Vermont

Private, rural retreat nestled in the Green Mountains of VT. Enjoy hiking trails, hot tub under the stars, huge fire pit and flower/vegetable gardens only 5 miles from Williams College, the Clark...

Created on Jun 16, 2024
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Rupert (4)

6 Br Villa Vacation Rental In Rupert, Vermont

Nestled in a serene valley of the Green Mountain National Forest and boasting 5 acres of maple tree-laden land, this Victorian home is the place for an unparalleled retreat. The 6-bedroom, 3.5-bath...

Created on Jun 16, 2024
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Shaftsbury (8)

1 Br Private Vacation Home Vacation Rental In Shaftsbury, Vermont

Spend the month, week or weekend in a beautiful rustic converted barn on 6.5 very private sunny country acres with southerly long-range views of Mt. Anthony and the Bennington Monument. Wander the...

Created on Jun 16, 2024
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Stamford (3)

4 Br Private Vacation Home Vacation Rental In Stamford, Vermont

Located in the heart of Southern Vermont at the end of an unpaved road, Senecal Farms is a charming four bedroom farmhouse in a spectacular setting. Built in 1865, this traditional home is ideal...

Created on Jun 16, 2024
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West Rupert (4)

4 Br Lodge Vacation Rental In Ripton, Vermont

Escape to River Stone Lodge in Vermont's Green Mountains for a memorable retreat! With a cozy living spaces, game room, hot tub, and scenic trails nearby, it's the perfect getaway for relaxation...

Created on Jun 16, 2024
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