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 Hartford
5.0 out of 5 average rating, 19 reviewsCozy, Renovated Quechee Treehouse
Dec 7 – 14
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
Apr 13 – 20
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Dec 26 – Jan 2
Home in Hartford
5.0 out of 5 average rating, 35 reviewsLuxury Lodge Oasis Near Dartmouth and Ski Resorts
Oct 23 – 30
Home in Killington
5.0 out of 5 average rating, 28 reviews* Slope Side Sauna w/ Shuttle *
Sep 18 – 25
Home in Norwich
5.0 out of 5 average rating, 11 reviewsLuxury Countryside Escape - pool, pond, any more!
Jan 25 – Feb 1
Home in Springfield
4.98 out of 5 average rating, 61 reviewsLuxury Mid-Century Modern Vermont Home, Okemo View
Oct 15 – 22
Home in Mendon
4.92 out of 5 average rating, 12 reviewsJam House:Renovated Luxury+Pool+Land+Hot Tub+Sauna
Oct 25 – Nov 1
Condo rentals with a pool
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Aug 19 – 26
Condo in Killington
4.93 out of 5 average rating, 107 reviewsLocation! Cozy 2BR Condo - Mountain Side
Oct 29 – Nov 5
Condo in Mendon
4.88 out of 5 average rating, 100 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Nov 1 – 8
Condo in Killington
4.83 out of 5 average rating, 120 reviewsCharming 3 Bedroom 2 Bath Ski Home/Off
Oct 16 – 23
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Jun 27 – Jul 4
Condo in Killington
4.85 out of 5 average rating, 242 reviewsComfy ski in/out studio at base of Pico-Killington
Jul 9 – 16
Condo in Killington
4.82 out of 5 average rating, 148 reviewsSkier's Retreat 2bed/1.5 bath condo w/ Amenities
Aug 16 – 23
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Jan 3 – 10
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