
Holiday rentals in Windsor County
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Top-rated holiday rentals in Windsor County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Windsor County holiday rentals
Other great holiday rentals in Windsor County
Guest favourite

Cottage in Reading
4.9 out of 5 average rating, 78 reviewsStone Wall Cottage, Stonewall : GMHA, Okemo
Guest favourite

Home in Woodstock
5 out of 5 average rating, 16 reviewsFabulous Log Home in the Woods
Top guest favourite

Cottage in Bridgewater
4.98 out of 5 average rating, 52 reviewsRiverside Cottage - Bridgewater Vermont
Guest favourite

Cabin in Bridgewater
4.98 out of 5 average rating, 55 reviews500 Acre Farm Retreat: OQ Farm's Priory
Top guest favourite

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

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

Cottage in Hartland
4.99 out of 5 average rating, 84 reviewsPrivate cottage perched on Lull's Brook
Top guest favourite

Flat in Woodstock
5 out of 5 average rating, 28 reviewsHilltop Hideaway in Woodstock
Destinations to explore
- Rentals with an EV charger Windsor County
- Rentals with a sauna Windsor County
- Rentals with lake access Windsor County
- Rentals with a hot tub Windsor County
- Rentals with a washing machine and dryer Windsor County
- Apartment rentals Windsor County
- Rentals with an accessible-height toilet Windsor County
- Rentals with a fireplace Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Rentals with a kayak Windsor County
- Waterfront rentals Windsor County
- Cottage rentals Windsor County
- Beachfront rentals Windsor County
- Villa rentals Windsor County
- Rentals with an accessible-height bed Windsor County
- Farm stay rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with a firepit Windsor County
- Rentals with a patio Windsor County
- Townhouse rentals Windsor County
- Pet-friendly rentals Windsor County
- Guest house rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Flat rentals Windsor County
- Family-friendly rentals Windsor County
- Rentals with breakfast Windsor County
- Family-friendly rentals Windsor County
- Tiny house rentals Windsor County
- Rentals with pools Windsor County
- Rentals with beach access Windsor County
- Bed and breakfasts Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Bretwood Golf Course
- Fox Run Golf Club
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Crotched Mountain Ski and Ride
- Hooper Golf Course
- Cozy Cottages & Otter Valley Winery
- Ekwanok Country Club
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
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