
Holiday rentals with a pool in Woodstock
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woodstock
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Popular amenities for Woodstock rentals with a pool
House rentals with a pool

Golf, Bike, Fish, or Hike!
Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Beautiful & Bright Eastman Home
Beautiful and spacious home. Everything was clean and at any point I would message Denise she would respond right away. The area was beautiful as well. I would definitely book her home again.

Charming Sugarbush Standalone Condo
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
We thoroughly enjoyed our stay at the Big Red house in New London! The host, Chris, was so helpful in working with our dates. We traveled to New London for my mother-in-law's celebration of life, and I could not think of a better place to stay with my family and close family friends. The children (and adults!) enjoyed the game room and other amenities such as the screened porch and hot tub. We would have used the sauna/cold plunge if we had more time. The house was spacious, comfortable, and very private but easy access and close to downtown New London which was perfect for us. Again, I must highlight how gracious and helpful the host was - it was one of the best experiences I had so far with Airbnb. Please consider staying here - you will love it!

Bright & Modern Quechee Town House - Self Check-In
We stayed at Michael’s place for 5 nights for our son’s graduation at Dartmouth. It’s a very comfortable house in a nice quiet location in cul-de-sac so there were no outside noises. The beds were comfortable, we slept well, there was enough room to spread out for everyone. We loved the proximity to Woodstock and Quchee gorge. And getting to Hanover to campus was an easy 20 minute drive. Michael is a great host! Very responsive and helpful. Thank you !

Comfortable, relaxing large country home
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

Cozy, Renovated Quechee Treehouse
We stayed in Jill's house for a ladies' weekend away, centered around the Covered Bridges Half Marathon. The house was easy to find, as described, and a convenient 5-10 minute drive to anywhere we wanted to go all weekend. The driveway was easy to navigate, even with the 4 cars we ended up arriving in. Jill was quick to respond with answers to any questions. The house was clean, spacious and cozy, with plenty of space to hang out both indoors and out. The beds were comfortable, and the small amenities including paper towels, laundry detergent, bug spray, etc., were nice to have on hand. Would stay again!
Apartment rentals with a pool

Comfy ski in/out studio at base of Pico-Killington
Apartment was clean including the bathroom, just as described by the listing. The place was very comfortable to stay at.

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤
Jared was very helpful and responsive, seemed like he was waiting for us to check in to make sure everything was ok. The place was very clean, spacious and got everything we needed. Highly recommend!

Cozy Slopeside Studio at Pico
After being disappointed by the weather (lack of snow), we were SO happy we chose to stay here with Cole and Rachel. We spent most of our time cuddled on the couch watching movies and felt right at home. We loved it!

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!
My family and I had an awesome stay in Tina's apartment. We took full advantage of the outdoor pool and the indoor spa space, which were both fantastic. The unit was a clean, cozy and comfortable place to return to at the end of busy days. Tina was an exceptional host - one of the most responsive/helpful experiences I've had with an Airbnb host. We would definitely stay here again!

Condo on Quechee Golf Course with Private Feel
What an amazing house!! Well stocked and cozy! Sweeping views of the Quechee golf club welcome you in the backyard. And a river to boot. Absolute heaven. Plus Corey is one of the most responsive hosts I’ve worked with.

Modern Killington Farmhouse Condo: Close to Resort
Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.

Serene Top Floor Condo (resort style amenities)
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
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- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Owl's Nest Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Dorset Field Club
- Autumn Mountain Winery
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Fox Run Golf Club