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 Ludlow
5.0 out of 5 average rating, 4 reviewsNEW Guest Cottage on 23 Acres
Cottage in Woodstock
5.0 out of 5 average rating, 25 reviews2 person SunCottage - Hot Tub Solar Geothermal
Cottage in Plymouth
5.0 out of 5 average rating, 27 reviewsNirvanaSanctuary~Dogs~FirePlace&Pit~HotTub~Okemo
Cottage in Bridgewater
4.97 out of 5 average rating, 146 reviewsNewly Renovated, Hot tub, 2min to Killington lift
Cottage in Plymouth
5.0 out of 5 average rating, 32 reviewsGoodWoods~Okemo~Killington~Dogs~HotTub~Fireplace
Cottage in Bridgewater
4.96 out of 5 average rating, 24 reviewsCountry Chalet, HotTub, 8 Mins to Skyeship Gondola
Cottage in Killington
4.84 out of 5 average rating, 56 reviews5BR w hot tub 3 miles from Killington Mountain
Pet-friendly cottage rentals
Cottage in Chester
4.9 out of 5 average rating, 63 reviewsQuaint stone house!
Cottage in Londonderry
4.83 out of 5 average rating, 36 reviewsVermont Country Cottage (Near Village)
Cottage in Weston
4.83 out of 5 average rating, 81 reviewsBirch Hollow Cottage: a riverside Vermont retreat
Cottage in Hartford
4.89 out of 5 average rating, 18 reviewsThe Carriage House on Main
Cottage in Peru
4.88 out of 5 average rating, 88 reviewsThe Vermont Pond House
Cottage in Reading
4.95 out of 5 average rating, 131 reviewsShattuck Hill Cottage
Cottage in Ludlow
4.8 out of 5 average rating, 10 reviews2BR lakefront with dock, swim platform, & firepit
Cottage in Woodstock
4.51 out of 5 average rating, 37 reviewsCozy 2BR Riverfront Dog Friendly | Deck | Firepit
Private cottage rentals
Cottage in Peru
4.95 out of 5 average rating, 66 reviewsMoon Beam Cottage--A cozy and welcoming retreat
Cottage in Woodstock
4.94 out of 5 average rating, 33 reviewsGlobetrotter Retreat - Countryside Carriage House
Cottage in Fairlee
4.89 out of 5 average rating, 9 reviewsLake Fairlee Porch Views from The Edgevale Gem
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
Cottage in Woodstock
4.95 out of 5 average rating, 134 reviewsVail Cottage
Cottage in Reading
4.9 out of 5 average rating, 59 reviewsStone Wall Cottage: GMHA, Woodstock VT, Okemo
Cottage in Norwich
4.75 out of 5 average rating, 16 reviewsRiverfront Cozy Cottage near Dartmouth College
Cottage in Acworth
5.0 out of 5 average rating, 14 reviewsClassic lakeside cottage with gorgeous sunset view
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- Cottage rentals Vermont
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- Rentals with a washer and dryer Windsor County
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