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
4.88 out of 5 average rating, 50 reviewsKillington Ski Condo: Your Winter Escape!
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 Hartford
4.94 out of 5 average rating, 18 reviews4 bedroom Farmhouse w/ Peloton & spacious yard
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
Home in Hartford
4.87 out of 5 average rating, 46 reviewsQuechee Mountain Home w/Jacuzzi, Gym and Game Room
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
4.95 out of 5 average rating, 56 reviewsBright & Cozy ski in condo with fireplace & views
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
4.9 out of 5 average rating, 134 reviews2 bed-2 bath (6 max): walk to lifts and lodges
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
Condo in Ludlow
5 out of 5 average rating, 19 reviewsJackson Gore/Okemo Ski-in/Out Slopeside Studio
Destinations to explore
- Rentals with pools United States
- Rentals with pools Vermont
- Rentals with pools Vermont
- Rentals with pools New York
- Rentals with pools New Hampshire
- Farmstay rentals Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Rentals with a fire pit Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with lake access Windsor County
- Rentals with breakfast Windsor County
- Fitness-friendly rentals Windsor County
- Villa rentals Windsor County
- Monthly Rentals Windsor County
- Pet-friendly rentals Windsor County
- Apartment rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Waterfront rentals Windsor County
- Townhouse rentals Windsor County
- Rentals with a sauna Windsor County
- Beachfront rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Cottage rentals Windsor County
- Tiny house rentals Windsor County
- Rentals with an EV charger Windsor County
- Family-friendly rentals Windsor County
- Rentals with a kayak Windsor County
- Rentals with beach access Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Condo rentals Windsor County
- Rentals with a hot tub Windsor County
- Bed and breakfasts Windsor County
- Kid-friendly rentals Windsor County
- Rentals with outdoor seating Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with a patio Windsor County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Food and drink United States
- Entertainment United States
- Sightseeing United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States
- Things to do Vermont
- Food and drink Vermont
- Things to do Windsor County
- Food and drink Windsor County