Cottage vacation rentals in Windsor County
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Top-rated cottage rentals in Windsor County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County cottage rentals
Cottage rentals with a hot tub
Cottage in Plymouth
4.96 out of 5 average rating, 23 reviewsCute Cool Cabin! Plymouth, Vermont.
Cottage in Plymouth
5 out of 5 average rating, 32 reviewsGoodWoods~Okemo~Killington~Dogs~HotTub~Fireplace
Cottage in Woodstock
5 out of 5 average rating, 28 reviews2 person SunCottage - Hot Tub Solar Geothermal
Cottage in Killington
4.83 out of 5 average rating, 59 reviews5BR w hot tub 3 miles from Killington Mountain
Cottage in Bridgewater
4.96 out of 5 average rating, 24 reviewsCountry Chalet, HotTub, 8 Mins to Skyeship Gondola
Cottage in Bridgewater
4.97 out of 5 average rating, 180 reviewsNewly Renovated, Hot tub, 2min to Killington lift
Cottage in Ludlow
4.81 out of 5 average rating, 26 reviews3BR lakefront with dock, swim platform, & firepit
Cottage in Barnard
5 out of 5 average rating, 17 reviewsAndas Hus: Little Luxury
Pet-friendly cottage rentals
Cottage in Reading
4.95 out of 5 average rating, 151 reviewsShattuck Hill Cottage
Cottage in Mendon
New place to stayThe Mendon Cottage: Cozy Home. Killington / Pico
Private room in Strafford
5 out of 5 average rating, 6 reviews“Matisse” bedroom in a country cottage
Cottage in Mount Holly
4.98 out of 5 average rating, 58 reviewsCozy COTTAGE- ski, swim, hike, foliage, near Okemo
Cottage in Londonderry
4.85 out of 5 average rating, 53 reviewsVermont Country Cottage (Near Village)
Cottage in Chester
5 out of 5 average rating, 16 reviewsHaven for Nature Lovers, Pet Owners, Skiers
Cottage in Hartford
4.89 out of 5 average rating, 18 reviewsThe Carriage House
Cottage in Woodstock
4.43 out of 5 average rating, 42 reviewsCozy 2BR Riverfront Dog Friendly | Deck | Firepit
Private cottage rentals
Cottage in Peru
4.96 out of 5 average rating, 72 reviewsMoon Beam Cottage--A cozy and welcoming retreat
Cottage in Weston
4.97 out of 5 average rating, 94 reviewsCharming Mountain Cottage **NO CLEANING FEE**
Cottage in Cavendish
4.86 out of 5 average rating, 7 reviewsCharming Cavendish Cottage: All-Season Retreat!
Cottage in Woodstock
4.94 out of 5 average rating, 149 reviewsVail Cottage
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
Cottage in Fairlee
4.82 out of 5 average rating, 17 reviewsLake Fairlee Porch Views from The Edgevale Gem
Cottage in Vershire
4.92 out of 5 average rating, 87 reviewsThe Vershire Fortress
Cottage in Woodstock
4.95 out of 5 average rating, 141 reviewsThe Cottage on Westerdale Road
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