
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

Fish, Bike, Golf, or Hike!

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

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

Luxury Condo - with Garage Parking and Pool

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Perfect 2 Bedroom Ski Escape at Killington

Cozy Slopeside Studio at Pico

PeeP Colors 2 Bedrm only 1/2 mile to Mtn & Apres

One Bedroom Suite Near Okemo

#45 Luxury Ski & Summer Condo with Private Sauna

2 Bedroom Condo in Quechee, VT
Other vacation rentals with a pool

Swirl Suite at Killington: Remodeled 2RM/2BA Suite

Winter is upon us!

Ski-in Ski-Out Cozy Mountainside Condo

Bright & Cozy Ski Home Condo with Mountain Views

Sweet Retreat

The Woods Renovated 1BR Studio close to the slopes

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

Cozy Studio Apartment
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- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Dorset Field Club
- Hooper Golf Course
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Ekwanok Country Club
- Montshire Museum of Science
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Whaleback Mountain
- Brattleboro Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Food and drink Vermont
- Nature and outdoors Vermont
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