
Holiday rentals with a pool in Windsor County
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Top-rated rentals with a pool in Windsor County
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Holiday rentals for every style
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Popular amenities for Windsor County rentals with a pool
House rentals with a pool

Fish, Bike, Golf, or Hike!

Quaint 2 bedroom Condominium

Ski-In/Ski-Out Hike Okemo Mountain Condo

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

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

Comfy ski in/out studio at base of Pico-Killington

Perfect 2 Bedroom Ski Escape at Killington

Bright & Cozy Ski Home Condo with Mountain Views

Winterplace - Steps away from Slopes

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

Condo on Quechee Golf Course with Private Feel

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

#45 Luxury Ski & Summer Condo with Private Sauna
Other holiday rentals with a pool

Late-Summer Getaway | Quechee Club Access

Villa with Pool + Fitness Center Access

Sweet Retreat

The Swell Annex: Studio w/ Kitchenette, Pool. 641

Book Peep Golf Bike Hike 2 Bedrm at Mtn & Apres

Cozy Quechee Corner Cabin

Elegant 3BR with Fireplace & Shuttle to Slopes

Cozy Studio Condo on Bus Rte to Killington Resort!
Destinations to explore
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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
- Fox Run Golf Club
- Ekwanok Country Club
- Lucky Bugger Vineyard & Winery
- Mount Sunapee Resort
- Stratton Mountain Resort
- Brattleboro Ski Hill
- 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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