
Villa vacation rentals in Windsor County
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Top-rated villa rentals in Windsor County
Guests agree: these villas 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 villa rentals
Private villa rentals

Trail Creek 11 is on a ski home trail

Pico D305 located slope side at Pico quiet area

Villa with Pool + Fitness Center Access

Base of Killington with Sports center access

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Vermont Villa Near the Trails

Villa with a Fireplace Near the Trails

Pico C103 located at the base of Pico Mountain
Luxury villa rentals

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Whiffletree B8 Great location with shuttle bus to

Base of Killington with Sports center access

Sunrise Timberline I4
Villa rentals with a pool

Sunrise East Glade C8

Whiffletree B8 Great location with shuttle bus to

Villa with Pool + Fitness Center Access

Sunrise Timberline I7

Whiffletree base of Killington outdoor pool

Whiffletree base of Killington outdoor pool

Base of Killington with Sports center access

Whiffletree base of Killington outdoor pool
Destinations to explore
- Rentals with an accessible height bed Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Fort Ticonderoga
- Mount Snow Ski Resort
- Dartmouth Skiway
- Tenney Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Dorset Field Club
- Stratton Mountain Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Bretwood Golf Course
- Crotched Mountain Ski and Ride
- Autumn Mountain Winery
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Northeast Slopes Ski Tow
- Veterans Memorial Recreation Area Ski Hill
- Baker Hill Golf Club
- Ragged Mountain Resort
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
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- Nature and outdoors Vermont
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes