Vacation 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.
Vacation 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
Home in Killington
Ski, Bike, Golf, or Hike!
Home in Norwich
Luxury Countryside Escape - pool, pond, any more!
Home in Chittenden
Comfortable, relaxing large country home
Home in Woodstock
Dana Road House Sunlit VT Country Home w/HotTub
Home in Killington
Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Home in Hartford
Cozy, Renovated Quechee Treehouse
Home in Bridgewater
Luxurious family retreat home in the mountains
Home in Springfield
Luxury Mid-Century Modern Vermont Home, Okemo View
Condo rentals with a pool
Condo in Killington
Cozy & Convenient Ski Home Condo
Condo in Mendon
105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Condo in Killington
#45 Mountain Ski & Summer Condo with Private Sauna
Condo in Killington
Comfy ski in/out studio at base of Pico-Killington
Condo in Killington
A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Condo in Killington
Location! Cozy 2BR Condo - Mountain Side
Condo in Killington
Charming 3 Bedroom 2 Bath Ski Home/Off
Condo in Ludlow
Enjoy a Ski-On/Ski-Off Okemo Ski Getaway
Destinations to explore
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