
Vacation rentals in Windsor County
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Top-rated vacation rentals in Windsor County
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Popular amenities for Windsor County vacation rentals
Other great vacation rentals in Windsor County
Guest favorite

Cottage in Reading
4.9 out of 5 average rating, 78 reviewsStone Wall Cottage, Stonewall : GMHA, Okemo
Top guest favorite

Farm stay in Clarendon
5 out of 5 average rating, 69 reviewsDream Catcher Farm
Top guest favorite

Guesthouse in Woodstock
5 out of 5 average rating, 69 reviewsLuxury & Privacy in Woodstock - Barn at Rose Hill
Top guest favorite

Home in Windsor
4.99 out of 5 average rating, 96 reviewsStylish Ascutney Cabin •View •Chef’s Kitchen •Pets
Guest favorite

Tiny home in Ludlow
5 out of 5 average rating, 27 reviewsAlpine Reflection + Hot Tub
Guest favorite

Barn in Bridgewater
5 out of 5 average rating, 79 reviewsBreathtaking Riverfront Farmhouse w/Mountain Views
Top guest favorite

Apartment in Sharon
4.98 out of 5 average rating, 57 reviewsVermont Suite @Anderson-Key Farm
Top guest favorite

Home in West Windsor
4.94 out of 5 average rating, 50 reviewsChuck's Place
Destinations to explore
- Rentals with outdoor seating 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
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Dorset Field Club
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Bretwood Golf Course
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- Veterans Memorial Recreation Area Ski Hill
- Crotched Mountain Ski and Ride
- Hooper Golf Course
- Things to do Windsor County
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- Family travel hub Tips and inspiration
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- 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