Discover a selection of 1,500 vacation rentals in Windsor County that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $150 per night, and condos and cabins are popular options for a stay in Windsor County. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Windsor County
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How many vacation rentals are available around Windsor County?

Our 2021 property listings offer a large selection of 1,473 vacation rentals around Windsor County. From 495 condo and apartment rentals to 134 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Windsor County

Ludlow
652 vacation rentals
Quechee
84 vacation rentals
Bethel
674 vacation rentals
Windsor
260 vacation rentals
Springfield
163 vacation rentals
Norwich
115 vacation rentals
Hartland
169 vacation rentals
Chester
921 vacation rentals
Weston
873 vacation rentals
Barnard
147 vacation rentals
Cavendish
413 vacation rentals
Plymouth
1,005 vacation rentals
Rochester
148 vacation rentals
South Woodstock
529 vacation rentals
White River Junction
109 vacation rentals
Woodstock
806 vacation rentals
Bridgewater
865 vacation rentals
Bridgewater Corners
984 vacation rentals
Stockbridge
931 vacation rentals
Brownsville
230 vacation rentals