
Vacation rentals with a pool in Winhall
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winhall
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 Winhall rentals with a pool
House rentals with a pool

Country hideaway
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

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!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

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!

The Brick House on Washington Street
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

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!

Idyllic Dorset Home: Serene Escape w/amazing views
My group of 9 had a wonderful stay here! The house was very spacious, clean, and modern and accurately represented in the posting. John was extremely responsive during our process and proactively checked in with us to ensure we were able to check-in to the property smoothly. We had a small issue with one of the stove top burners and when we reached out to John, he followed up immediately to resolve the issue. I highly recommend staying here!

Your country home awaits! Pool, tennis, Dogs loved
Great place to stay if you plan to ski or snowboard at Stratton. Close to the center of Manchester (grocery store, shops, etc . . .).
Condo rentals with a pool

Dog-Friendly Mountainside Escape/Pool/AC
Beautiful condo, nice location near the Sunrise lift and Bear Mountain. Very home like atmosphere in condo.

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.

Slopes N Seasons | Trailside Condo at Mount Snow
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.

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

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

New - walk to Mt Snow w/ Tub & Gym
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!

Stratton Duplex Condo Steps to Lifts, Village!
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.

Mt. Snow Condo with Pool-Hot Tubs-Sauna MTN Views
Had a lovely stay at Leah’s condo. Very comfy and cozy and super close to Mt Snow!
Quick stats about vacation rentals with a pool in Winhall
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Hudson Valley Vacation rentals
- Boston Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Plainview Vacation rentals
- Cape Cod Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Fitness-friendly rentals Winhall
- Apartment rentals Winhall
- Rentals with a washer and dryer Winhall
- Rentals with outdoor seating Winhall
- Rentals with a fire pit Winhall
- Chalet rentals Winhall
- Rentals with lake access Winhall
- Family-friendly rentals Winhall
- Townhouse rentals Winhall
- Rentals with a fireplace Winhall
- Rentals with a hot tub Winhall
- Condo rentals Winhall
- Rentals with a patio Winhall
- Pet-friendly rentals Winhall
- Ski-in/ski-out rentals Winhall
- Cabin rentals Winhall
- House rentals Winhall
- Rentals with a sauna Winhall
- Kid-friendly rentals Winhall
- Rentals with pools Bennington County
- Rentals with pools Vermont
- Rentals with pools 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
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Monadnock State Park
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Lake George Expedition Park
- Hooper Golf Course
- Bretwood Golf Course
- Baker Hill Golf Club
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Willard Mountain
- Northern Cross Vineyard
- Gooney Golf