
Holiday 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.
Holiday 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

Golf, Bike, Fish, or Hike!

Hilltop 9-BR Mountain Retreat 5-min to Okemo

Ski-In/Ski-Out Hike Okemo Mountain Condo

The Fairway House - Premier Golf Course 3 BR Home

Dana Road House Sunlit VT Country Home w/HotTub

Bright & Modern Quechee Town House - Self Check-In

Private Farmhouse with in ground pool!
Apartment rentals with a pool

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

Book now to Golf Fish Hike Bike Vemont!

Bright & Cozy condo with AC, Tennis, and Pool

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

Bike Golf hike pool Tennis 2 Bedrm at Mtn & Apres

Winterplace - Steps away from Slopes

One Bedroom Suite Near Okemo

Serene Top Floor Condo (resort style amenities)
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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
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