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
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Popular amenities for Windsor County rentals with a pool
House rentals with a pool
Home in Killington
4.88 out of 5 average rating, 51 reviewsKillington Ski Condo: Your Winter Escape!
Home in Hartford
5 out of 5 average rating, 23 reviewsLuxury Home w/ Hot Tub - close to Quechee Club
Home in Ludlow
5 out of 5 average rating, 3 reviewsOkemo Condo - Ski In/Out
Home in Hartford
4.82 out of 5 average rating, 22 reviewsYour Vermont Vacation Awaits!
Home in Woodstock
4.96 out of 5 average rating, 57 reviewsDana Road House Sunlit VT Country Home w/HotTub
Home in Bridgewater
4.89 out of 5 average rating, 46 reviewsLuxurious family retreat home in the mountains
Home in Hartford
4.88 out of 5 average rating, 32 reviewsCozy, Renovated Quechee Treehouse
Home in Hartford
4.87 out of 5 average rating, 15 reviewsElegance Meets Rustic Charm: Vermont 3-Bed Retreat
Condo rentals with a pool
Condo in Killington
4.98 out of 5 average rating, 41 reviewsLuxury Ski Condo - with Garage Parking and Pool
Condo in Killington
4.85 out of 5 average rating, 254 reviewsComfy ski in/out studio at base of Pico-Killington
Condo in Mendon
4.88 out of 5 average rating, 101 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Condo in Killington
4.85 out of 5 average rating, 82 reviews1 BR Best Location w/ Pools/Massage Chair/Hottub!
Condo in Killington
4.98 out of 5 average rating, 42 reviewsFun 2 BR | 2 BA Condo - Pool/Spa - Walk to Lift
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Quechee
4.89 out of 5 average rating, 73 reviews2 Bedroom Condo in Quechee, VT
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
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