Discover a selection of 1,500 vacation rentals in Windsor County, US 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 kitchens. Prices start at $240 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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How many vacation rentals are available around Windsor County, US?

Our 2020 property listings offer a large selection of 1,420 vacation rentals around Windsor County. From 488 condo and apartment rentals to 82 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Windsor County?

There are many lovely places to stay for a holiday trip or just for a weekend in Windsor County. From Vrbo travelers, the top most popular destinations to visit are:

  • Ludlow: 653 vacation rentals
  • Okemo Mountain Resort: 517 vacation rentals
  • Quechee: 99 vacation rentals
  • Chester: 918 vacation rentals
  • Weston: 925 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Windsor County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Windsor County?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Windsor County:

  • Ludlow: 653 rentals
  • Chester: 918 rentals
  • Weston: 925 rentals
  • Barnard: 184 rentals
  • Cavendish: 478 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Windsor County?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Windsor County are:

  • Hartness State Airport (VSF): 688 vacation rentals
  • Rutland State Airport (RUT): 1,046 vacation rentals
  • Lebanon Municipal Airport (LEB): 273 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Windsor County?

Vrbo offers a large selection of rentals near lovely places in Windsor County. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Quechee Gorge: 547 rentals
  • Jackson Gore Ski Resort at Okemo: 699 rentals
  • Silver Lake State Park: 744 rentals
  • Mount Ascutney: 779 rentals
  • White River Junction Station: 264 rentals

But there are many other points of interest around Windsor County listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Windsor County

Ludlow
653 vacation rentals
Chester
918 vacation rentals
Weston
925 vacation rentals
Barnard
184 vacation rentals
Cavendish
478 vacation rentals
Plymouth
932 vacation rentals
Norwich
137 vacation rentals
Rochester
147 vacation rentals
Woodstock
720 vacation rentals
Springfield
165 vacation rentals
Bridgewater
769 vacation rentals
Stockbridge
831 vacation rentals
Andover
611 vacation rentals
Windsor
304 vacation rentals
Hartland
204 vacation rentals
Sharon
176 vacation rentals
South Royalton
191 vacation rentals
Pomfret
198 vacation rentals
Reading
839 vacation rentals
Bethel
557 vacation rentals