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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.

Vermont Mountainside Cabin- Nature +  Epic Views
SUPERHOST
Entire cabin · 2 guests · 1 bed · 1 bathroom

Vermont Mountainside Cabin- Nature + Epic ViewsPLEASE READ THE FULL DESCRIPTION, & FEEL FREE TO GET IN TOUCH WITH ANY QUESTIONS - THANKS This cozy, mountainside cabin is the perfect place to relax and reconnect with friends, family, and nature. The house is nestled in the heart of the Green Mountains, and feels a world away from the hustle and bustle of everyday life. And if you feel like driving to town, our corner of southern Vermont offers a host of outdoor recreation, dining, arts, and more.

Bright Wings mini-farm and pollinator sanctuary
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom

Bright Wings mini-farm and pollinator sanctuaryThe space at Bright Wings is light-filled and serene, a quiet place to base your Vermont adventures. Awake to bird song and spend your days in the outdoors or discovering unique local arts & crafts. Then come back to Bright Wings "nightlife": listen to owls, star gaze, watch deer graze or read one of the many mysteries. Cairo and I enjoy meeting new people and sharing our view. All are welcome here.

NEW Escape the City- Vermont Studio
SUPERHOST
Entire flat · 2 guests · 1 bed · 1 bathroom

NEW Escape the City- Vermont StudioOur newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Holiday rentals for every style

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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

  1. Entire cabin
  2. Arlington
The Sheep Shack - a cozy Vermont cabin
SUPERHOST
  1. Entire guest house
  2. Arlington
Cottage with a View
SUPERHOST
  1. Entire cottage
  2. Shaftsbury
Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
SUPERHOST
  1. Entire flat
  2. Bennington
Cooper's Place
SUPERHOST
  1. Entire guest house
  2. Arlington
Cozy Log Cabin Suite (New Construction)
SUPERHOST
  1. Entire cottage
  2. Shaftsbury
Rollin Cottage
SUPERHOST
  1. Entire guest house
  2. Dorset
Seven Springs Barn Nestled in the Heart of Dorset
SUPERHOST
  1. Private room
  2. Manchester
Private suite with room to spread out.
SUPERHOST
  1. Entire flat
  2. Bennington
The Octopus's Garden
SUPERHOST
  1. Entire guest house
  2. Manchester
At River's Edge
  1. Entire guest suite
  2. Manchester Center
Manchester Ctr. Guest House w/ Balcony & Mt. Views
SUPERHOST
  1. Entire cabin
  2. Shaftsbury
The Vermont Dream Cabin on 70 Private Acres