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
May 22 – 29
Cottage in Woodstock
5.0 out of 5 average rating, 25 reviews2 person SunCottage - Hot Tub Solar Geothermal
Mar 19 – 26
Cottage in Bridgewater
4.97 out of 5 average rating, 145 reviewsNewly Renovated, Hot tub, 2min to Killington lift
Oct 8 – 15
Cottage in Plymouth
5.0 out of 5 average rating, 32 reviewsGoodWoods~Okemo~Killington~Dogs~HotTub~Fireplace
Oct 21 – 28
Cottage in Killington
4.84 out of 5 average rating, 56 reviews5BR w hot tub 3 miles from Killington Mountain
Sep 3 – 10
Cottage in Bridgewater
4.96 out of 5 average rating, 24 reviewsCountry Chalet, HotTub, 8 Mins to Skyeship Gondola
Mar 18 – 25
Pet-friendly cottage rentals
Cottage in Chester
4.92 out of 5 average rating, 60 reviewsQuaint stone house!
Apr 26 – May 3
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 23 – 30
Cottage in Hartford
4.88 out of 5 average rating, 17 reviewsThe Carriage House on Main
Mar 20 – 27
Cottage in Weston
4.83 out of 5 average rating, 80 reviewsBirch Hollow Cottage: a riverside Vermont retreat
Dec 20 – 27
Cottage in East Bethel
4.68 out of 5 average rating, 268 reviewsApple Branch Guest House
Jul 24 – 31
Cottage in Peru
4.88 out of 5 average rating, 88 reviewsThe Vermont Pond House
Aug 11 – 18
Cottage in Reading
4.95 out of 5 average rating, 128 reviewsShattuck Hill Cottage
Nov 5 – 12
Private cottage rentals
Cottage in Weston
4.97 out of 5 average rating, 91 reviewsCharming Mountain Cottage **NO CLEANING FEE**
Oct 14 – 21
Cottage in Peru
4.95 out of 5 average rating, 66 reviewsMoon Beam Cottage--A cozy and welcoming retreat
Jun 20 – 27
Cottage in Ludlow
5.0 out of 5 average rating, 22 reviewsCome for the fresh snow; stay for the eclipse!
May 6 – 13
Cottage in Fairlee
4.89 out of 5 average rating, 9 reviewsLake Fairlee Porch Views from The Edgevale Gem
Mar 2 – 9
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
Feb 2 – 9
Cottage in Woodstock
4.95 out of 5 average rating, 134 reviewsVail Cottage
Sep 18 – 25
Cottage in Reading
4.9 out of 5 average rating, 58 reviewsStone Wall Cottage: GMHA, Woodstock VT, Okemo
Jan 18 – 25
Cottage in Norwich
4.75 out of 5 average rating, 16 reviewsRiverfront Cozy Cottage near Dartmouth College
May 25 – Jun 1
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