Plan for peace of mind

Some properties allow cancellations up to 14 days before arrival. Check the policy before booking.

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Where to stay near Windsor County?

Our 2020 accommodation listings offer a large selection of 1,592 holiday rentals near Windsor County. From 720 Houses to 559 Condos/Apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Windsor County is on HomeAway.

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

There are many lovely places to stay for a long holiday or just a weekend break in Windsor County. From HomeAway travellers, the popular destinations to visit are:

  • West Windsor: 863 holiday rentals
  • Okemo Mountain Resort: 544 holiday rentals
  • Weston: 975 holiday rentals
  • Ludlow: 733 holiday rentals
  • Chester: 1,016 holiday rentals

HomeAway offers you the possibility to discover many other popular destinations in Windsor County! Please use our search bar to access the selection of holiday rentals available in other popular destinations.

What are the main cities to discover in Windsor County?

Whether you are travelling solo or with family and friends, here are the cities in Windsor County with the largest selection of holiday rentals for a perfect city break:

  • Weston: 975 holiday homes
  • Ludlow: 733 holiday homes
  • Chester: 1,016 holiday homes
  • Hartland: 209 holiday homes
  • Barnard: 195 holiday homes

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

Can I find easy access holiday homes when travelling by plane to Windsor County?

Yes of course. Our owners offer a large selection of holiday homes near to airports. Airports with a large selection of rentals in Windsor County are:

  • Lebanon Municipal Airport (LEB): 282 holiday houses
  • Rutland State Airport (RUT): 1,280 holiday houses
  • Edward F Knapp State Airport (MPV): 490 holiday houses

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

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

HomeAway offers a large selection of holiday homes near great places to visit in Windsor County. From HomeAway travellers, the more popular points of interest to stay for a holiday trip or just for a weekend are:

  • Marsh-Billings-Rockefeller National Historical Park: 1,379 holiday rentals
  • Woodstock Town Hall Theatre: 1,393 holiday rentals
  • Paradise Park: 798 holiday rentals
  • Vermont River Tubing: 910 holiday rentals
  • Windsor Station: 798 holiday rentals

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

Explore destinations around Windsor County

Weston
975 holiday rentals
Ludlow
733 holiday rentals
Chester
1,016 holiday rentals
Hartland
209 holiday rentals
Barnard
195 holiday rentals
Woodstock
964 holiday rentals
Rochester
155 holiday rentals
Cavendish
500 holiday rentals
Bridgewater
1,025 holiday rentals
Bethel
786 holiday rentals
Windsor
321 holiday rentals
Plymouth
1,188 holiday rentals
Andover
632 holiday rentals
Perkinsville
359 holiday rentals
Norwich
149 holiday rentals
Springfield
175 holiday rentals
Stockbridge
1,091 holiday rentals
South Royalton
208 holiday rentals
Sharon
187 holiday rentals
Reading
1,013 holiday rentals