Vacation rentals in Bennington County
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Top-rated vacation rentals in Bennington County
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Vacation rentals for every style
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Popular amenities for Bennington County vacation rentals
Other great vacation rentals in Bennington County
Guest favorite
Cottage in Jamaica
4.82 out of 5 average rating, 464 reviewsForest Cottage ~ 7min to Stratton, Private, Views
May 8 – 15
$95 per night
Guest favorite
Apartment in Wilmington
4.88 out of 5 average rating, 279 reviewsGlobetrotter Retreat - Minutes to the Mountain
Sep 22 – 29
$94 per night
Guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 140 reviewsBeautiful Timber Frame Retreat
Sep 13 – 20
$192 per night
Guest favorite
Cabin in Shaftsbury
4.99 out of 5 average rating, 200 reviewsThe Hygge Loft- mid-mod cabin on 70 forested acres
Nov 2 – 9
$287 per night
Guest favorite
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Apr 13 – 20
$81 per night
Superhost
Cabin in Shaftsbury
4.9 out of 5 average rating, 381 reviewsThe LoveNest -Charming private cabin on 65 acres
Aug 22 – 29
$144 per night
Superhost
Cabin in Sandgate
4.92 out of 5 average rating, 127 reviewsVermont Mountainside Cabin- Nature + Epic Views
Dec 29 – Jan 5
$138 per night
Guest favorite
Apartment in Pownal
4.94 out of 5 average rating, 180 reviewsThe Shepherd's Retreat
May 3 – 10
$95 per night
Destinations to explore
- Rentals with pools Bennington County
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- Rentals with a fireplace Bennington County
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- Rentals with beach access Bennington County
- Rentals with a sauna Bennington County
- Farmstay rentals Bennington County
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- Condo rentals Bennington County
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- Rentals with a patio Bennington County
- House rentals Bennington County
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- Kid-friendly rentals Bennington County
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