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House holiday rentals in Windsor County
Find and book unique houses on Airbnb
Top-rated house rentals in Windsor County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Windsor County
House rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-705865629746917495/original/a5001518-ab29-41f5-8515-b113737d00d0.jpeg?im_w=720)
Home in Killington
4.99 out of 5 average rating, 107 reviewsSugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-915078301974185050/original/e7980533-9620-41ab-a00d-9f17f7516906.jpeg?im_w=720)
Home in Norwich
5 out of 5 average rating, 16 reviewsLuxury Countryside Escape - pool, pond, any more!
![](https://a0.muscache.com/im/pictures/miso/Hosting-923854349715405208/original/d827f2e8-2b4d-48a8-8aae-858441a67c05.png?im_w=720)
Home in Hartford
5 out of 5 average rating, 23 reviewsCozy, Renovated Quechee Treehouse
![](https://a0.muscache.com/im/pictures/miso/Hosting-837765164954943319/original/4cfaeae8-25ae-4b2c-b405-fd3e43ea2b24.jpeg?im_w=720)
Home in Hartford
4.89 out of 5 average rating, 37 reviewsQuechee Mountain Home w/Jacuzzi, Gym and Game Room
![](https://a0.muscache.com/im/pictures/91085253-7851-426b-94e2-4b40b92b5125.jpg?im_w=720)
Home in Bridgewater
4.91 out of 5 average rating, 43 reviewsLuxurious family retreat home in the mountains
![](https://a0.muscache.com/im/pictures/miso/Hosting-25623925/original/a7800a8f-4c44-458a-8a34-5cd8b70278e8.jpeg?im_w=720)
Home in Chittenden
4.9 out of 5 average rating, 82 reviewsComfortable, relaxing large country home
![](https://a0.muscache.com/im/pictures/91ca0e2d-46f8-474c-b8f5-2f54d57aae4e.jpg?im_w=720)
Home in Woodstock
4.96 out of 5 average rating, 56 reviewsDana Road House Sunlit VT Country Home w/HotTub
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Home in Killington
4.98 out of 5 average rating, 57 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Weekly house rentals
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Home in Chester
5 out of 5 average rating, 18 reviewsCozy 1850 farmhouse in Stone Village of Chester
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Home in Woodstock
5 out of 5 average rating, 24 reviewsWoodstock Village Retreat
![](https://a0.muscache.com/im/pictures/miso/Hosting-553662949137286568/original/22aea2ad-c5bc-44d5-8047-fc83d762739e.jpeg?im_w=720)
Home in Woodstock
4.97 out of 5 average rating, 36 reviewsCheerful 3-bedroom home close to village center
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Home in Woodstock
4.98 out of 5 average rating, 52 reviewsThe DeerBrook, Distinctive Vermont Lodging
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Home in Andover
5 out of 5 average rating, 31 reviewsAmazing Views and Sunsets
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Home in Woodstock
5 out of 5 average rating, 13 reviewsGreat Maples
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Home in Windsor
5 out of 5 average rating, 58 reviewsGreat Summer Getaway- rustic modern view house
![](https://a0.muscache.com/im/pictures/miso/Hosting-24367083/original/7fe4fceb-6cc0-4c9e-8d4f-4a4d49c90ccb.png?im_w=720)
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsPet Friendly Woodstock Home; Riverside Getaway!
Private house rentals
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Home in Ludlow
5 out of 5 average rating, 40 reviewsFresh and Cozy Ski House - Hot Tub and Fireplace!
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Home in Woodstock
4.97 out of 5 average rating, 32 reviewsHilltop Homestead: Charming Farmhouse & Gardens
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Home in Thetford
5 out of 5 average rating, 40 reviewsPop's Lodge
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Home in Woodstock
5 out of 5 average rating, 18 reviewsGrange Hall, South Woodstock Historic Home
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Home in Pittsfield
4.93 out of 5 average rating, 43 reviewsHideaway Mountain at Killington
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1026813159775904332/original/f7dba511-b044-42e2-a9e0-0f5f033dcb97.jpeg?im_w=720)
Home in Charlestown
5 out of 5 average rating, 16 reviewsNewly Renovated Private Comfy Farmhouse
![](https://a0.muscache.com/im/pictures/d4f8940c-d0fd-4427-8cec-572e0926c6a8.jpg?im_w=720)
Home in Woodstock
4.95 out of 5 average rating, 39 reviewsHiker’s Hygge on 21 Acres and Aqueduct Trails
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Home in Hartford
4.97 out of 5 average rating, 93 reviewsLuxury Barn w/ Hot Tub, Sauna & Panoramic Views
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