
Vacation rentals with a pool in Windham County
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Top-rated rentals with a pool in Windham County
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Popular amenities for Windham County rentals with a pool
House rentals with a pool

Hiking Pet Retreat I Game RM l ChimneyHill l Pool
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!

Private chalet tucked in the green mountains
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!

Outdoor Enthusiasts Paradise!
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!

6 BR Perfect Private Retreat in Vermont!
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

Brand New 4 Bedroom Listing with private hot tub!
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!

The Villa - Industrial Farmhouse with Hot Tub
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!

Ski and tennis house by Stratton Ski Resort.
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!

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

Mount Snow Ski Chalet
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.

Renovated Condo - 5 min walk to Mount Snow
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

3BR/3BA Hearthstone condo with pool access
Great location in Stratton Village . The condo was perfect and had everything we needed .

Perfect 3 Br. Getaway Condo in Stratton, Vermont!
Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!

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

Stratton two bedroom condo on a shuttle
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.

A Village location, Steps to the Lifts & Village
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!

Pool & hot tub! Hiking, nature and mountain views!
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!
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Berkshire East Mountain Resort
- Mount Greylock Ski Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Hildene, The Lincoln Family Home
- Bretwood Golf Course
- Hooper Golf Course
- Brattleboro Ski Hill
- Dorset Field Club
- Fox Run Golf Club
- Baker Hill Golf Club
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