
Holiday rentals with a pool in Windsor County
Find and book unique homes with a pool on Airbnb
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
Get the amount of space that is right for you
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

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!

Killington Vistas: Luxury 4BR Ski On/Off. Hot Tub.
Apartment rentals with a pool

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

Perfect 2 Bedroom Ski Escape at Killington

Killington Swell Suite: 2RM/2BA Condo|. Pool. 642

True Ski in/Ski out with Pool, Hot tubs & Firepits

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

Special prices Bike Hike 2 Bedrm at Mtn & Apres

Winterplace - Steps away from Slopes

Condo on Quechee Golf Course with Private Feel
Other holiday rentals with a pool

Winter is upon us!

Ski-in Ski-Out Cozy Mountainside Condo

Bright & Cozy Ski Home Condo with Mountain Views

The Woods Renovated 1BR Studio close to the slopes

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

Cozy Killington Condo

Cozy Studio Apartment

Vermont Villa Near the Trails
Destinations to explore
- Cabin rentals Windsor County
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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
- Dartmouth Skiway
- Ragged Mountain Resort
- Stratton Mountain Resort
- Dorset Field Club
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Hooper Golf Course
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Ekwanok Country Club
- Fox Run Golf Club
- Autumn Mountain Winery
- Whaleback Mountain
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Nature and outdoors Vermont
- Food and drink Vermont
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