Vacation rentals in Bennington County

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Top-rated vacation rentals in Bennington County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Tiny homes in Wilmington
Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!
Jul. 18 – 25
$323 CAD per night
4.98 out of 5 average rating, 116 reviews
Guest favourite
Cabin in Jamaica
New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.
Apr. 24 – May 1
$207 CAD per night
4.99 out of 5 average rating, 175 reviews
Guest favourite
Cabin in Shaftsbury
The Hygge Loft- mid-mod cabin on 70 forested acres
The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!
Sep. 24 – Oct. 1
$519 CAD per night
4.99 out of 5 average rating, 193 reviews

Popular amenities for Bennington County vacation rentals

Other great vacation rentals in Bennington County

Guest favourite
Cabin in Shaftsbury
The LoveNest -Charming private cabin on 65 acres
Jun. 2 – 9
$225 CAD per night
4.9 out of 5 average rating, 377 reviews
Guest favourite
Home in Bennington
Cozy Modern Sugar House with spectacular views.
Dec. 1 – 8
$454 CAD per night
4.99 out of 5 average rating, 231 reviews
Guest favourite
Cottage in Shaftsbury
Rollin Cottage
May 4 – 11
$220 CAD per night
4.96 out of 5 average rating, 109 reviews
Guest favourite
Home in Sunderland
MOUNTAIN NEST, views, Manchester, hot tub,
May 4 – 11
$711 CAD per night
4.97 out of 5 average rating, 208 reviews
Guest favourite
Apartment in Manchester
Private two-bedroom suite within a two-story house
5.0 out of 5 average rating, 133 reviews
Guest favourite
Guest suite in Shaftsbury
Country Getaway with a Spa/Birds of a Feather Farm
Jul. 30 – Aug. 6
$219 CAD per night
4.98 out of 5 average rating, 128 reviews
Guest favourite
Home in Shaftsbury
Quintessential Vermont Country Home on 140 acres.
May 3 – 10
$362 CAD per night
4.99 out of 5 average rating, 271 reviews
Superhost
Cottage in Sunderland
Green Mountain Retreat
Apr. 7 – 14
$222 CAD per night
4.88 out of 5 average rating, 149 reviews
Guest favourite
Chalet in Dover
A charming VT chalet
Dec. 15 – 22
$250 CAD per night
4.92 out of 5 average rating, 253 reviews
Guest favourite
Tiny homes in Jamaica
Forest Cabin ~ 7min to Stratton, Cozy, Private
Apr. 12 – 19
$144 CAD per night
4.89 out of 5 average rating, 340 reviews
Guest favourite
Apartment in Manchester
Style and Comfort- Perfect Year Round Location
May 16 – 23
$231 CAD per night
4.99 out of 5 average rating, 166 reviews
Guest favourite
Apartment in Bennington
NEW Escape the City- Vermont Studio
Nov. 23 – 30
$144 CAD per night
4.93 out of 5 average rating, 153 reviews

Destinations to explore