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Holiday rentals in Bennington County

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Top-rated holiday rentals in Bennington County

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

Cooper's Place
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Cooper's PlaceSmall bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with Vermont flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the sitting porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas. One dog allowed.
The Hygge Loft- mid-mod cabin on 70 forested acres
SUPERHOST
Entire cabin · 2 guests · 1 bed · 1 bathroom
The Hygge Loft- mid-mod cabin on 70 forested acresThe Vermont Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping on an espresso or pour-over coffee while listening to a vinyl record, cozy up with snuggly blankets to watch a movie or play a game, stargaze while sitting by the fire on the private deck, or snuggle up in the comfy king-sized bed with the views of treetops and sky all around. It’s the kind of place you never want to leave and we hope you'll love!
Cozy & Bright Chalet near Mt Snow ◌ over the moon
Entire chalet · 5 guests · 4 beds · 1 bathroom
Cozy & Bright Chalet near Mt Snow ◌ over the moonWarm, cozy, and bright. Waiting for you to enjoy the outdoors however you'd like. Walking distance to restaurants and shops, and the Moover shuttle stop is just a stone's throw away -- skip the Mount Snow parking lot! Our chalet is close enough to what you need yet far enough away to offer you some peace and quiet.

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Popular amenities for Bennington County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Bennington County

SUPERHOST
  1. Entire cottage
  2. Dorset
Pond Cottage
$202 SGD per night
  1. Entire chalet
  2. Wilmington
NEW! Mtn. View Retreat: 5 Mi to MT Snow, Hot Tub
$444 SGD per night
  1. Entire chalet
  2. Londonderry
Peaceful Chalet In Londonderry
$189 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Dover
West Dover Village River View
$182 SGD per night
  1. Entire residential home
  2. Winhall
Charming, cozy ski cabin. Great location!
$532 SGD per night
SUPERHOST
  1. Entire residential home
  2. Bennington
The Old Academy
$369 SGD per night
SUPERHOST
  1. Entire residential home
  2. Bennington
Southern Vermont Home
$245 SGD per night
SUPERHOST
  1. Entire residential home
  2. Bennington
Cozy Modern Sugar House with spectacular views.
$353 SGD per night
SUPERHOST
  1. Entire residential home
  2. Shaftsbury
Quintessential Vermont Country Home on 140 acres.
$242 SGD per night
SUPERHOST
  1. Entire cottage
  2. Shaftsbury
Rollin Cottage
$175 SGD per night
  1. Entire residential home
  2. Wardsboro
Mtn House w/Hot Tub & Game Room- Mt. Snow/Stratton
$415 SGD per night
SUPERHOST
  1. Entire cottage
  2. Woodford
Willow Tree Cottage on Peaceful Mountain Lake
$262 SGD per night