Vacation rentals with a pool in Windham County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Windham 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 Windham County rentals with a pool
House rentals with a pool
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Home in Wardsboro
5.0 out of 5 average rating, 11 reviewsSheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
Home in Wilmington
4.91 out of 5 average rating, 22 reviewsMountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Home in Dover
5.0 out of 5 average rating, 19 reviewsSpring getaway@Mt snow, West Dover VT
Home in Wardsboro
5.0 out of 5 average rating, 31 reviewsSummer getaway! Hot Tub, Fire Pit, Game Room, AC!
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
Home in Wardsboro
5.0 out of 5 average rating, 7 reviews3 bedroom 10 minutes to mt snow 20 to Stratton
Home in Dover
4.94 out of 5 average rating, 31 reviewsLuxury King Suite, fireplace, bunkbed- Farmhouse 4
Condo rentals with a pool
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Condo in Dover
4.77 out of 5 average rating, 91 reviewsCozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Condo in Dover
5.0 out of 5 average rating, 36 reviewsFour Seasons Slope-side Getaway at Mount Snow
Condo in Dover
4.94 out of 5 average rating, 53 reviewsMt. Snow Dream Mtn View+Fireplace!
Condo in Dover
4.96 out of 5 average rating, 23 reviewsSki in Ski out condo great location
Condo in Dover
5.0 out of 5 average rating, 16 reviewsLyon Family Lodge
Condo in Stratton
4.98 out of 5 average rating, 55 reviewsStratton Mtn in Summer! Golf, tennis, bike, swim!
Condo in Dover
4.88 out of 5 average rating, 86 reviews⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷
Destinations to explore
- Rentals with pools United States
- Rentals with pools Boston
- Rentals with pools Vermont
- Rentals with pools New York
- Rentals with pools New Hampshire
- Apartment rentals Windham County
- Rentals with a patio Windham County
- Rentals with breakfast Windham County
- Rentals with beach access Windham County
- House rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with a hot tub Windham County
- Rentals with an EV charger Windham County
- Fitness-friendly rentals Windham County
- Chalet rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with a kayak Windham County
- Rentals with lake access Windham County
- Rentals with a fire pit Windham County
- Rentals with a fireplace Windham County
- Bed and breakfasts Windham County
- Private suite rentals Windham County
- Townhouse rentals Windham County
- Rentals with a sauna Windham County
- Pet-friendly rentals Windham County
- Condo rentals Windham County
- Farmstay rentals Windham County
- Guesthouse rentals Windham County
- Tiny house rentals Windham County
- Cabin rentals Windham County
- Monthly Rentals Windham County
- Beachfront rentals Windham County
- Family-friendly rentals Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Rentals with a washer and dryer Windham County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes