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
Sep 3 – 10
Cottage in Woodstock
5.0 out of 5 average rating, 25 reviews2 person SunCottage - Hot Tub Solar Geothermal
Jan 26 – Feb 2
Cottage in Bridgewater
4.97 out of 5 average rating, 145 reviewsNewly Renovated, Hot tub, 2min to Killington lift
Sep 18 – 25
Cottage in Plymouth
5.0 out of 5 average rating, 32 reviewsGoodWoods~Okemo~Killington~Dogs~HotTub~Fireplace
Sep 2 – 9
Cottage in Killington
4.84 out of 5 average rating, 56 reviews5BR w hot tub 3 miles from Killington Mountain
Oct 14 – 21
Pet-friendly cottage rentals
Cottage in Chester
4.9 out of 5 average rating, 61 reviewsQuaint stone house!
Dec 16 – 23
Cottage in Weston
4.83 out of 5 average rating, 81 reviewsBirch Hollow Cottage: a riverside Vermont retreat
Nov 8 – 15
Cottage in Rochester
4.98 out of 5 average rating, 58 reviewsCozy cottage near Killington & Sugarbush
Dec 27 – Jan 3
Cottage in Londonderry
4.83 out of 5 average rating, 36 reviewsVermont Country Cottage (Near Village)
Sep 24 – Oct 1
Cottage in East Bethel
4.68 out of 5 average rating, 268 reviewsApple Branch Guest House
Jul 20 – 27
Cottage in Hartford
4.88 out of 5 average rating, 17 reviewsThe Carriage House on Main
Mar 22 – 29
Cottage in Peru
4.88 out of 5 average rating, 88 reviewsThe Vermont Pond House
Aug 13 – 20
Cottage in Reading
4.95 out of 5 average rating, 128 reviewsShattuck Hill Cottage
Nov 9 – 16
Private cottage rentals
Cottage in Peru
4.95 out of 5 average rating, 66 reviewsMoon Beam Cottage--A cozy and welcoming retreat
May 14 – 21
Cottage in Fairlee
4.89 out of 5 average rating, 9 reviewsLake Fairlee Porch Views from The Edgevale Gem
Mar 2 – 9
Cottage in Ludlow
5.0 out of 5 average rating, 22 reviewsCome for the fresh snow; stay for the eclipse!
May 11 – 18
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
Oct 28 – Nov 4
Cottage in Woodstock
4.95 out of 5 average rating, 134 reviewsVail Cottage
Sep 20 – 27
Cottage in Reading
4.9 out of 5 average rating, 58 reviewsStone Wall Cottage: GMHA, Woodstock VT, Okemo
Aug 4 – 11
Cottage in Acworth
5.0 out of 5 average rating, 14 reviewsClassic lakeside cottage with gorgeous sunset view
Apr 1 – 8
Cottage in Norwich
4.75 out of 5 average rating, 16 reviewsRiverfront Cozy Cottage near Dartmouth College
Jun 16 – 23
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