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Cottage holiday rentals in Windsor County
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Windsor County
Guests agree: these cottages 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 cottage rentals in Windsor County
Cottage rentals with a hot tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-884735708127916336/original/d7b94bd3-afb1-40fa-bfd0-407bba66d909.jpeg?im_w=720)
Cottage in Ludlow
5 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1096313695079272670/original/29649841-ff21-46de-bb9c-e721df2dafac.jpeg?im_w=720)
Cottage in Barnard
5 out of 5 average rating, 5 reviewsAndas Hus: Little Luxury
![](https://a0.muscache.com/im/pictures/miso/Hosting-40866986/original/6ef745e8-26f6-44c7-90b6-ea5989ced66d.jpeg?im_w=720)
Cottage in Woodstock
5 out of 5 average rating, 28 reviews2 person SunCottage - Hot Tub Solar Geothermal
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Cottage in Ludlow
4.82 out of 5 average rating, 17 reviews2BR lakefront with dock, swim platform, & firepit
![](https://a0.muscache.com/im/pictures/miso/Hosting-23562663/original/5ae24add-3d86-4402-9529-422045278492.jpeg?im_w=720)
Cottage in Plymouth
4.96 out of 5 average rating, 23 reviewsCute Cool Cabin! Plymouth, Vermont.
Pet-friendly cottage rentals
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Cottage in Chester
4.91 out of 5 average rating, 68 reviewsQuaint stone house!
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Cottage in Londonderry
4.84 out of 5 average rating, 43 reviewsVermont Country Cottage (Near Village)
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Cottage in Rochester
4.98 out of 5 average rating, 63 reviewsCozy cottage near Killington & Sugarbush
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Cottage in Hartford
4.89 out of 5 average rating, 18 reviewsThe Carriage House on Main
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Cottage in Peru
4.88 out of 5 average rating, 88 reviewsThe Vermont Pond House
![](https://a0.muscache.com/im/pictures/66e45799-4413-44df-bcf0-dda01fab89a3.jpg?im_w=720)
Cottage in Reading
4.95 out of 5 average rating, 136 reviewsShattuck Hill Cottage
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Cottage in Chester
5 out of 5 average rating, 13 reviewsHaven for Nature Lovers, Pet Owners, Skiers
![](https://a0.muscache.com/im/pictures/17673727/0000d077_original.jpg?im_w=720)
Cottage in Mount Holly
4.98 out of 5 average rating, 57 reviewsCozy COTTAGE- ski, swim, hike, foliage, near Okemo
Private cottage rentals
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Cottage in Fairlee
4.9 out of 5 average rating, 10 reviewsLake Fairlee Porch Views from The Edgevale Gem
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Cottage in Newport
4.97 out of 5 average rating, 96 reviewsLake House at Breezy Point
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Cottage in Peru
4.96 out of 5 average rating, 68 reviewsMoon Beam Cottage--A cozy and welcoming retreat
![](https://a0.muscache.com/im/pictures/miso/Hosting-51732901/original/d507bbd1-c857-4253-a662-d0ffebe18c8d.jpeg?im_w=720)
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
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Cottage in Woodstock
4.95 out of 5 average rating, 138 reviewsVail Cottage
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Cottage in Woodstock
4.95 out of 5 average rating, 137 reviewsThe Cottage on Westerdale Road
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Cottage in Vershire
4.92 out of 5 average rating, 85 reviewsThe Vershire Fortress
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Cottage in Acworth
5 out of 5 average rating, 17 reviewsClassic lakeside cottage with gorgeous sunset view
Destinations to explore
- Cottage rentals Vermont
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- Rentals with a washing machine and dryer Windsor County
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