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
5.0 out of 5 average rating, 30 reviews* Slope Side Sauna w/ Shuttle *
Home in Killington
4.98 out of 5 average rating, 46 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Home in Woodstock
4.98 out of 5 average rating, 53 reviewsDana Road House Sunlit VT Country Home w/HotTub
Home in Hartford
5.0 out of 5 average rating, 20 reviewsCozy, Renovated Quechee Treehouse
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Home in Hartford
5.0 out of 5 average rating, 35 reviewsLuxury Lodge Oasis Near Dartmouth and Ski Resorts
Home in Springfield
4.93 out of 5 average rating, 87 reviewsSki Mountain View Estate
Home in Springfield
4.98 out of 5 average rating, 61 reviewsLuxury Mid-Century Modern Vermont Home, Okemo View
Condo rentals with a pool
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Condo in Killington
4.83 out of 5 average rating, 121 reviewsCharming 3 Bedroom 2 Bath Ski Home/Off
Condo in Killington
4.85 out of 5 average rating, 242 reviewsComfy ski in/out studio at base of Pico-Killington
Condo in Killington
4.93 out of 5 average rating, 107 reviewsLocation! Cozy 2BR Condo - Mountain Side
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Killington
4.82 out of 5 average rating, 149 reviewsSkier's Retreat 2bed/1.5 bath condo w/ Amenities
Condo in Mendon
4.88 out of 5 average rating, 100 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Destinations to explore
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