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Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

Farm stay in Plainfield
Renovated 1817 Hobby Farm Close to Dartmouth
Come stay at our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. It is a daily work in progress, gardening and taking care of the chickens and sheep, so it is not perfect, but it is lively and ever-changing. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.
$113 per night
Apartment in Weathersfield
The Loft at Weathersfield
Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.
$140 per night
Cabin in West Windsor
Sunset Cabin - your private romantic hideaway
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just a few minutes from Mt. Ascutney's hiking and mountain-biking trails and in the middle of fantastic cycling country. WiFi now available! Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring Vermont.
$140 per night

Stay near Windsor's top sights

Mt Ascutney State Park19 locals recommend
Harpoon Brewery Taproom and Beer Garden125 locals recommend
Cornish-Windsor Covered Bridge28 locals recommend
Windsor Station Restaurant & Barroom33 locals recommend
Pizza Chef15 locals recommend
Windsor Diner7 locals recommend

Other great vacation rentals in Windsor

Apartment in Lebanon
Green Street Hideaway. Downtown Lebanon.
$88 per night
Guesthouse in Hartland
Yurt In The Woods - Private Refuge
$169 per night
Cabin in West Windsor
Cowshed Cabin Farm & Stable
$128 per night
Cottage in Hartland
Breeze Hill Cottage
$125 per night
Guesthouse in Hartland
Cottage for Two/Solo Getaway/Musician's Retreat
$162 per night
Guesthouse in Springfield
Connecticut River-Cozy Cottage
$101 per night
Apartment in Lebanon
The Old Farmhouse
$86 per night
Apartment in Weathersfield
Cute VT Bungalow With 180 Degree View of NH
$150 per night
Cabin in Mailing Address: Windsor
Fat Sheep Farm & Cabins - Sunrise Cabin
$189 per night
Home in West Windsor
Birdie's Nest Guesthouse
$130 per night
Home in Windsor
Modern custom home, mountain views on Mt Ascutney
$354 per night
Tiny home in West Windsor
Red Barn Cabin
$168 per night

Quick stats about vacation rentals in Windsor

Total rentals

30 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

1.8K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Windsor