
Vacation rentals with a pool in Windsor County
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Top-rated rentals with a pool in Windsor County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windsor County rentals with a pool
House rentals with a pool

Pond, Pool, Mountain Views | Au Bout du Chemin

Quaint 2 bedroom Condominium

Ski-In/Ski-Out Hike Okemo Mountain Condo

Luxe 4BR w Incredible View & Game Room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

The Fairway House - Premier Golf Course 3 BR Home

Premier Quechee Newton Village Condo: Pet Friendly

Dana Road House Sunlit VT Country Home w/HotTub
Condo rentals with a pool

Killington Tree House: 2 Room Modern Condo 432

Perfect 2 Bedroom Ski Escape at Killington

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Winterplace - Steps away from Slopes

Condo on Quechee Golf Course with Private Feel

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Charming 3 Bedroom 2 Bath Ski Home/Off

Walk to lift, Ski home, Sunny with loft
Other vacation rentals with a pool

Come to Killington this summer!

Golf Fish Hike Bike Vemont Foliage season!

The Woods Renovated 1BR Studio close to the slopes

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Comfortable, relaxing large country home

Hotel Standard Condo Minutes from Okemo

Snowshed, Ramshead Ski Lodges in walking distance!

Vermont Villa Near the Trails
Destinations to explore
- Ski-in/ski-out rentals Windsor County
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- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Fort Ticonderoga
- Tenney Mountain Resort
- Dartmouth Skiway
- Dorset Field Club
- Ragged Mountain Resort
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Pico Mountain Ski Resort
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Whaleback Mountain
- Mount Snow Ski Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Mount Sunapee Resort
- Stratton Mountain Resort
- Brattleboro Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
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- Nature and outdoors Vermont
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