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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.

Renovated 1817 Hobby Farm Close to Dartmouth
SUPERHOST
Farm stay · 4 guests · 3 beds · 1 bath
Renovated 1817 Hobby Farm Close to DartmouthCome stay at our hobby farm in Plainfield Village! Experience country living with a 20 minute proximity to Hanover and Dartmouth University. It is a daily work in progress, gardening and taking care of the chickens and sheep, so it is never 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 take a hike in J.D. Salingers farm. Every season is beautiful here!
Firewheel Hill: Private, contemporary house
SUPERHOST
Entire residential home · 6 guests · 6 beds · 2.5 baths
Firewheel Hill: Private, contemporary houseFirewheel Hill House is nestled on a private road in the mountains of West Windsor Vermont. With modern amenities and a breathtaking view of Mount Ascutney; This house is the perfect getaway for you and your family to enjoy all this area has to offer. A network of bike and horse trails abuts the property. The house is ten minutes to GMHA, 20 minutes to Woodstock 30-40 minutes from Suicide Six and Okemo and less than an hour to Killington. You must have 4WD to stay here between December-April.
Ogden's Mill Farm
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bath
Ogden's Mill FarmPrivate guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Barn and stabling available for visiting horses.

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Popular amenities for Windsor vacation rentals

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

Other great vacation rentals in Windsor

  1. Entire condominium (condo)
  2. West Windsor
Lovely Trailside 2 Bedroom Condo
SUPERHOST
  1. Entire cabin
  2. Mailing Address: Windsor
Fat Sheep Farm & Cabins - Sunrise Cabin
SUPERHOST
  1. Entire guest suite
  2. West Windsor
Cute, clean and comfy 2 BR studio
  1. Entire residential home
  2. Plainfield
Historic Home on 17 acres of land. Go escape!
SUPERHOST
  1. Entire residential home
  2. West Windsor
Meadow View. 35 acres outside your door!
SUPERHOST
No reviews yet
  1. Entire residential home
  2. Windsor
Cozy Home for All Season Warmth and Fun
SUPERHOST
  1. Private room
  2. Hartland
Hartland Log Cabin
SUPERHOST
  1. Private room
  2. West Windsor
Newly renovated private space on Ascutney Trails
  1. Entire townhouse
  2. West Windsor
Cozy Condo for Skiing-Hiking-Biking Lovers
SUPERHOST
  1. Entire residential home
  2. Plainfield
The Oaks - secluded rural estate w/ amazing views
SUPERHOST
  1. Entire cabin
  2. Mailing Address: Windsor
Fat Sheep Farm & Cabins - Lull Brook Cabin
SUPERHOST
  1. Entire rental unit
  2. Hartland
Sunny Studio Apartment in Hartland