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Vacation rentals in Windsor

Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

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

  • Weaving Dreams Farm and Boutique
    SUPERHOSTPrivate room · 4 guests · 3 beds · 1 private bath
    Weaving Dreams Farm and Boutique

    200 year old Vt restored farmhouse. Working alpaca farm. Amazing views! Alpaca apparel and gifts available in the boutique. Friendly host. Close to Hanover, NH, Dartmouth, Woodstock. Ski Okemo Mt 45 min or Killington Mt 55 min. Easy access off I91.

    What guests are saying:

    “Laurens place was all she described it to be and then some. We were comfortable and truly at home as it offered so much. Charming is not a cliché here. We entered the boutique and were greeted by Lauren, Mojo her sweet pug mix, 2 cats and later were introduced to the alpacas. We cannot wait to go back!”

  • 1849 schoolhouse newly restored
    SUPERHOSTEntire house · 4 guests · 2 beds · 2 baths
    1849 schoolhouse newly restored

    Come and stay in this historic, beautifully restored one room schoolhouse on 5 acres. "Lil Red", a 2 bedroom, 2 bath home has been meticulously renovated and is cozy for 4. Come experience the beauty and history that is Windsor.

    What guests are saying:

    “Marylnn's place is GREAT for any family or solo traveler. The space is unlike anything I've ever seen and is spectacularly stocked with everything you'll need. If you have anyone who is struggling with stairs do not fear, the first bed room is downstairs as well as a bathroom. There is also a bathroom and bedroom up the stairs for those who are able. The space is not too far away from town and there's a fun llama farm practically next door. We stayed a day after it had snowed and woke up to some moose tracks on the back porch! Very exciting! We ventured down to the creek despite the snow, and had a fabulous time relaxing in the living room and dining area. The kitchen has everything you could need to cook and all the little things you don't think about (like paper towels and coffee filters). a MUST stay in Southern Vermont!”

  • Ogden's Mill Farm
    SUPERHOSTEntire cottage · 4 guests · 3 beds · 1 bath
    Ogden's Mill Farm

    Private 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.

    What guests are saying:

    “"Perfect" is an understatement. Our two high-energy young boys, my husband and I would have loved to have stayed the whole summer and more. The cabin was immaculate and equipped with everything a family could need. Top-notch appliances were a bonus! The sprawling property is breathtaking: rolling hills, an inviting pond with a diving board, trails to keep you busy for days, handcrafted birdhouses attracting a stunning range of birds to admire. Jamie and her husband know exactly how much interaction guests are looking for, and you'll have privacy if that's what you're there for. In our case, since we were all eager to learn about the property and the area, they were not just consummate hosts but companions. Our children were able to enjoy the horses, chickens and dogs with our hosts or on their own, and as hosts they went above and beyond giving recommendations for area attractions by guiding us to spots we never would have found on our own. We immediately booked another stay there this summer, and hope to return often in other seasons as well.”

Vacation rentals for every style

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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

Monet-Metcalf Cottage at The Butternuts
SUPERHOSTEntire guesthouse
Monet-Metcalf Cottage at The Butternuts
Price:$75 / night
Fat Sheep Farm & Cabins - Sunrise Cabin
SUPERHOSTEntire cabin
Fat Sheep Farm & Cabins - Sunrise Cabin
Price:$120 / night
Fitch Family Farm
Private room
Fitch Family Farm
Price:$60 / night
Fire Ridge Farm II
SUPERHOSTPrivate room
Fire Ridge Farm II
Price:$82 / night
"Good Night Moon Vintage" El Rey Glamping
SUPERHOSTPrivate room
"Good Night Moon Vintage" El Rey Glamping
Price:$42 / night
Green Street Hideaway
SUPERHOSTEntire apartment
Green Street Hideaway
Price:$95 / night
Upper Valley Home
SUPERHOSTPrivate room
Upper Valley Home
Price:$77 / night
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
SUPERHOSTPrivate room
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
Price:$29 / night
Firewheel Hill: Private, contemporary house
SUPERHOSTEntire house
Firewheel Hill: Private, contemporary house
Price:$126 / night
19th Century Bohemian Barn House
SUPERHOSTEntire house
19th Century Bohemian Barn House
Price:$250 / night
The Farmhouse at Gaelic Crossing
SUPERHOSTFarm stay
The Farmhouse at Gaelic Crossing
Price:$277 / night
LOG HOME APARTMENT IN WOODSTOCK VILLAGE
SUPERHOSTEntire apartment
LOG HOME APARTMENT IN WOODSTOCK VILLAGE
Price:$140 / night
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