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Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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

Sunrise over South Mountain
SUPERHOST
Entire loft · 4 guests · 2 beds · 1 bath

Sunrise over South MountainThis is a spacious guesthouse/retreat where you can relax and unwind. There are great views and walking down the road is serene, with open fields bordered by woods and teaming with wildlife. In the winter you can Nordic ski or snowshoe right outside your door, through fields and woodland paths through an active sugar-bush. We currently have guinea fowl and chickens as well as my friendly dog Annie who loves to play. We also have a kitty on the way (she's currently considering her options).

"Dragonfly Apartment" Private Bristol Apartment
SUPERHOST
Entire apartment · 3 guests · 1 bed · 1 bath

"Dragonfly Apartment" Private Bristol ApartmentVillage location in walking distance to everything...many local places to eat and shop. Also nearby are hiking trails and river swimming. 18 min to Middlebury, 19 min to Vergennes, 46 min to Burlington, 24 min to Mad River Glen, 30 min to Sugarbush.

Iconic "1795 House" in the heart of Vergennes
SUPERHOST
Entire apartment · 4 guests · 2 beds · 1 bath

Iconic "1795 House" in the heart of VergennesOur immaculate air-conditioned apartment is the perfect cozy getaway in the center of Vergennes, VT, “The Little City With a Big Heart”. Keypad check-in and the elevator provide easy and stainless private access. Walk one block through the Vergennes Green to shops and restaurants offering eat-in or take-out. You are also welcome to enjoy your morning coffee, a glass of wine, or an evening around the fire pit in our shaded backyard.

Vacation rentals for every style

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Popular amenities for Middlebury vacation rentals

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

Other great vacation rentals in Middlebury

SUPERHOST
  1. Entire guesthouse
  2. Middlebury
Centrally-located Victorian carriage house
  1. Entire apartment
  2. Vergennes
Little Brick House Off Main
SUPERHOST
  1. Entire cabin
  2. Rochester
Cozy, music filled cabin in spectacular setting!
SUPERHOST
  1. Entire cottage
  2. New Haven
Small New Haven Cozy Cottage
  1. Entire house
  2. Hancock
The Hancock House, a home in the mountains
SUPERHOST
  1. Entire house
  2. Middlebury
Nice one bedroom cottage
  1. Entire guesthouse
  2. Salisbury
Miss Dee's Retreat
  1. Entire guest suite
  2. Cornwall
Home Suite Home in Cornwall, Minutes from Midd!
SUPERHOST
  1. Entire apartment
  2. Bridport
Eagle's Landing
SUPERHOST
  1. Entire apartment
  2. Salisbury
Doc's Lake House 1st floor, 2 bdrm full apartment
SUPERHOST
  1. Entire house
  2. Vergennes
Little City Big Heart!!
SUPERHOST
  1. Entire house
  2. Leicester
Log Cabin Getaway near Middlebury and Green Mtns

Nearby destinations