Vacation rentals with a pool in Windham County

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windham County rentals with a pool

House rentals with a pool

Top guest favorite
Home in Wilmington
5 out of 5 average rating, 14 reviews

Hiking Pet Retreat I Game RM l ChimneyHill l Pool

LynnRating, 5 stars3 months ago
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!
Guest favorite
Home in Dover
5 out of 5 average rating, 14 reviews

Private chalet tucked in the green mountains

Zach & CourtneyRating, 5 stars2 months ago
Liz's place was the great! Beautiful, clean, and conveniently located to the mountain. Everything we needed for a long ski weekend with friends! Thank you!
Guest favorite
Home in Wilmington
5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars4 months ago
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!
Guest favorite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars10 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Superhost
Home in Dover
4.83 out of 5 average rating, 12 reviews

Brand New 4 Bedroom Listing with private hot tub!

EmilieRating, 5 stars5 months ago
We had the best ski trip staying at Todd’s place with our kids and family. The house has a great layout and is spacious, beautifully decorated, cozy, and well equipped with games. Location is great, 5 minutes from the slopes, and the shuttle can even pick you up from the driveway. Kids enjoyed the jacuzzi on the deck and the indoor swimming pool at the amenities center. Todd is super responsive and takes very good care of his guests. We highly recommend his place, thank you for everything!
Top guest favorite
Home in Dover
5 out of 5 average rating, 58 reviews

The Villa - Industrial Farmhouse with Hot Tub

StephanieRating, 5 stars4 months ago
We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!
Guest favorite
Home in Jamaica
4.96 out of 5 average rating, 25 reviews

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars3 months ago
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!
Superhost
Home in Wilmington
4.79 out of 5 average rating, 56 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!

CourtneyRating, 5 stars1 month ago
Stayed here as three couples with two dogs and had so much fun. We never left the home because it was so relaxing and enough to do right at the air bnb. Whether we were having a fire, going in the hot tub, playing pool, or making dinners together in the huge kitchen! We will definitely be back!

Condo rentals with a pool

Guest favorite
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Superhost
Condo in Dover
4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Christoph GRating, 5 stars2 months ago
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations
Guest favorite
Condo in Stratton Mountain
4.88 out of 5 average rating, 8 reviews

3BR/3BA Hearthstone condo with pool access

Jennifer CatherineRating, 5 stars2 months ago
Great location in Stratton Village . The condo was perfect and had everything we needed .
Guest favorite
Condo in Stratton
4.94 out of 5 average rating, 33 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

CarolineRating, 5 stars2 months ago
Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!
Guest favorite
Condo in Dover
4.96 out of 5 average rating, 45 reviews

Ski in/out - 2BR Condo - Indoor Pool/Spa

DanielleRating, 5 stars3 months ago
Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.
Guest favorite
Condo in Stratton
4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

DrewRating, 5 stars2 months ago
Megan’s place was great for a weekend of skiing at Stratton. Right on a shuttle route that picks you up at the front door and is very reliable. Clean and comfortable. Megan was extremely helpful and responsive throughout the whole process from booking to check in and check out.
Guest favorite
Condo in Stratton
4.98 out of 5 average rating, 46 reviews

A Village location, Steps to the Lifts & Village

LelahRating, 5 stars2 months ago
We loved staying at this property. The location is excellent for access to the village and the lifts. It is also cute to look out over the ice skating pond. It was clean, had all the kitchen amenities you would need to make food, and had fun ski-oriented decorations. It is also close to the hot tub and lounge area within the main building. It had everything we needed to make out ski weekend comfortable and memorable. Can't wait to stay again!
Guest favorite
Condo in Dover
4.89 out of 5 average rating, 9 reviews

Pool & hot tub! Hiking, nature and mountain views!

ToniRating, 5 stars2 months ago
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!

Destinations to explore