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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.

Rental unit in Bennington
Cozy Loft steps from VT downtown
This third floor loft apartment is walking distance from Historic Old Bennington and the downtown proper. Enjoy local shops and restaurants. Located a few minutes from the highway, giving you access to any number of ski slopes. This space offers high vaulted ceilings, sky lights and modern furnishings. A large bay window sitting area for plenty of natural light and a private balcony with views of Mount Anthony and the Monument. The space also has fiber Wi-Fi internet, Chromecast - YouTubeTV.
$101 per night
Cottage in Shaftsbury
Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have just added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 270 acre property.
$334 per night
Condo in Manchester
Lovely Condo in Manchester, VT.
Enjoy Manchester, VT at this centrally-located condo. Close to downtown outlet shops and restaurants! Located in a small, quiet and friendly condo complex ( unit 54). Guests can enjoy a fully equipped kitchen, 1 bedroom with a full size bed and an additional twin day bed in living room. Free parking in front of condo unit. Air conditioning, WiFi and a TV in the living room and bedroom. Host will provide linens and towels and is only a phone call away!
$115 per night

Other great vacation rentals in Bennington County

Cottage in Sunderland
Green Mountain Retreat
$152 per night
Cabin in Stratton
New Log Cabin 7 Min from Stratton Mtn!
$218 per night
Guesthouse in North Bennington
Birch House - lake, green trees + modern comforts
$102 per night
Rental unit in Dover
NEW! The Handle Studio!
$156 per night
Private room in Bennington
Leslie’s Bright & Cozy: Queen Room
$67 per night
Cabin in Manchester
Private Modern Rustic Loft
$149 per night
Cabin in Jamaica
New Cabin in Jamaica
$160 per night
Rental unit in Arlington
Brian Peace of Heaven
$130 per night
Condo in Stratton
Cozy condo within walking distance to the slopes.
$168 per night
Guesthouse in Arlington
Cozy Log Cabin Suite [100+ Reviews 4.98 Rating]
$125 per night
Rental unit in Manchester
Style and Comfort- Perfect Year Round Location
$129 per night
Cottage in North Bennington
Romantic Private Vermont Cottage - Waterfront
$159 per night