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.

Guest favorite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.
Apr 11 – 18
$135 per night
4.99 out of 5 average rating, 168 reviews
Superhost
Cabin in Wardsboro
Log Cabin Near Stratton/Mt Snow
Rustic log cabin for those looking for a getaway and a real Vermont experience. Pets allowed with *PET FEE* - add to your reservation There is Wifi &cell service (AT&T, Verizon). Please be aware this is not a luxury cabin, it is an authentic log cabin that we enjoy as a family during all seasons. No cable television - there is a TV with a Chromecast that you can use to stream from your phone over wifi. Firewood not provided 20 minutes to Stratton and 15 minutes to Mt. Snow
May 21 – 28
$129 per night
4.79 out of 5 average rating, 198 reviews
Guest favorite
Home in Wilmington
4 bedroom Ski House 15 min to Mount Snow
15 min to Mount Snow, 35 to Stratton! Come enjoy our 4 bedroom, 2 bathroom home in the charming Chimney Hill area of Wilmington, VT. This home is a perfect getaway for those looking for easy living, rest, relaxation, and family fun. The house has 4 bedrooms and comfortably sleeps 8 adults. Master bedroom has a King bed, and there is one Queen room, one Full room with a twin trundle, and one room with two Twin beds. There is also a pack n’ play available for use.
Sep 4 – 11
$183 per night
4.9 out of 5 average rating, 125 reviews

Popular amenities for Windham County rentals with a pool

House rentals with a pool

Guest favorite
Home in Wilmington
The Vermont Barn (Mount Snow)
Aug 26 – Sep 2
$277 per night
4.82 out of 5 average rating, 154 reviews
Guest favorite
Home in Wilmington
Adams Farm-"The Little Farmhouse"
Oct 26 – Nov 2
$298 per night
4.89 out of 5 average rating, 148 reviews
Guest favorite
Home in Peru
Beautiful Bromley/Manchester VT Retreat w/hot tub
Sep 16 – 23
$342 per night
4.92 out of 5 average rating, 138 reviews
Guest favorite
Home in Wilmington
Mountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Jul 4 – 11
$318 per night
4.89 out of 5 average rating, 18 reviews
Guest favorite
Home in Wardsboro
5BR Chalet, Hot Tub, Close to Mt Snow & Stratton
May 5 – 12
$320 per night
4.96 out of 5 average rating, 47 reviews
Guest favorite
Home in Wardsboro
Mt Snow/Stratton VT Getaway! w/Hot Tub + Game Room
Sep 29 – Oct 6
$709 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Home in West Dover
The Manor-Stunning Modern Farmhouse with Hot Tub
Apr 12 – 19
$740 per night
5.0 out of 5 average rating, 42 reviews
Superhost
Home in Wilmington
Stylish Chimney Hill Home - Close to Mt. Snow!
Sep 20 – 27
$227 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Dover
Seasons-Ski on/off. Access to all amenities
Mar 23 – 30
$209 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Home in Londonderry
Swim, ride, ski … repeat. Magic, Okemo, Stratton!
Nov 18 – 25
$796 per night
4.86 out of 5 average rating, 87 reviews
Guest favorite
Home in Wardsboro
3 bedroom 10 minutes to mt snow 20 to Stratton
Mar 14 – 21
$209 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Newfane
6 BR Perfect Private Retreat in Vermont!
Mar 6 – 13
$793 per night
4.91 out of 5 average rating, 46 reviews

Condo rentals with a pool

Guest favorite
Condo in Dover
Mt Snow Ski In/Out at Seasons
Jan 7 – 14
$338 per night
4.87 out of 5 average rating, 217 reviews
Superhost
Condo in Stratton
Perfect Location! Steps to Village and Mountain
Apr 1 – 8
$224 per night
4.89 out of 5 average rating, 104 reviews
Superhost
Condo in Dover
Cozy Mount Snow 1 Bed : Ski on/off, Hot tub, Deck
Apr 5 – 12
$74 per night
4.76 out of 5 average rating, 84 reviews
Guest favorite
Condo in Stratton
Premier Stratton Village Location - Pool & Hot Tub
Apr 5 – 12
$156 per night
4.95 out of 5 average rating, 84 reviews
Guest favorite
Condo in Dover
Cozy Mt Snow 1-bed w fireplace & view
Jul 17 – 24
$103 per night
4.93 out of 5 average rating, 30 reviews
Guest favorite
Condo in Dover
⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷
Aug 7 – 14
$128 per night
4.88 out of 5 average rating, 74 reviews
Guest favorite
Condo in Dover
Lyon Family Lodge
May 11 – 18
$126 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Condo in Stratton Mountain
Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!
Jan 8 – 15
$621 per night
5.0 out of 5 average rating, 46 reviews
Guest favorite
Condo in Dover
Ski in Ski out condo great location
Jul 3 – 10
$338 per night
4.93 out of 5 average rating, 14 reviews
Guest favorite
Condo in Stratton
Walk to lifts & Village,Year round pool&hot tubs
Apr 9 – 16
$442 per night
5.0 out of 5 average rating, 56 reviews
Guest favorite
Condo in Dover
Ski in/Out - Seasons on Mt Snow (renovated)
Jul 27 – Aug 3
$233 per night
4.9 out of 5 average rating, 69 reviews
Guest favorite
Condo in Dover
Winter Dream! The Handle Lodge at Snowtree Condos
May 15 – 22
$146 per night
4.99 out of 5 average rating, 96 reviews

Destinations to explore