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
4.98 out of 5 average rating, 46 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
May 10 – 17
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
Jan 30 – Feb 6
Home in Hartford
5.0 out of 5 average rating, 20 reviewsCozy, Renovated Quechee Treehouse
Feb 8 – 15
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Dec 28 – Jan 4
Home in Killington
5.0 out of 5 average rating, 29 reviews* Slope Side Sauna w/ Shuttle *
Sep 18 – 25
Home in Hartford
4.95 out of 5 average rating, 19 reviewsNew! Top of the Hill - 3 bd/2.5ba home!
Nov 7 – 14
Home in Hartford
5.0 out of 5 average rating, 35 reviewsLuxury Lodge Oasis Near Dartmouth and Ski Resorts
Oct 25 – Nov 1
Home in Springfield
4.98 out of 5 average rating, 61 reviewsLuxury Mid-Century Modern Vermont Home, Okemo View
Sep 3 – 10
Condo rentals with a pool
Condo in Killington
4.9 out of 5 average rating, 119 reviewsCozy & Convenient Ski Home Condo
Sep 2 – 9
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Aug 20 – 27
Condo in Killington
4.93 out of 5 average rating, 148 reviewsRenovated, w/Covered Parking-Shuttle-Walk to Lifts
Jul 10 – 17
Condo in Killington
4.83 out of 5 average rating, 120 reviewsCharming 3 Bedroom 2 Bath Ski Home/Off
Jun 18 – 25
Condo in Killington
4.93 out of 5 average rating, 107 reviewsLocation! Cozy 2BR Condo - Mountain Side
May 12 – 19
Condo in Mendon
4.88 out of 5 average rating, 100 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Aug 14 – 21
Condo in Killington
4.82 out of 5 average rating, 148 reviewsSkier's Retreat 2bed/1.5 bath condo w/ Amenities
Jul 30 – Aug 6
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Mar 18 – 25
Destinations to explore
- Rentals with pools United States
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