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Vacation rentals with a pool in Wardsboro

Find and book unique homes with a pool on Airbnb

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Popular amenities for Wardsboro rentals with a pool

House rentals with a pool

Top guest favorite
A private pool area is surrounded by lush greenery, featuring blue water under a clear sky. Poolside seating includes high-top chairs and a table set on a stone patio, accompanied by an umbrella for shade. A fire pit and additional seating are visible in the background.
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars8 months ago
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!
Superhost
The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars2 months ago
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.
Guest favorite
The spacious outdoor deck surrounds a circular swimming pool, inviting relaxation under the sky. A red railing complements the vibrant blue water. The two-story house, featuring large windows, stands in the background, framed by lush greenery and a clear blue sky.
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars8 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
The exterior of the townhome showcases a charming design with a steeply pitched roof and large arched windows. The property is situated on a well-maintained driveway surrounded by lush greenery and trees, enhancing the inviting atmosphere of this mountain retreat.
Home in Dover
4.83 out of 5 average rating, 12 reviews

Brand New 4 Bedroom Listing with private hot tub!

EmilieRating, 5 stars4 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!
Guest favorite
A serene pool area features a clear blue swimming pool surrounded by a concrete deck. Comfortable seating arrangements are positioned nearby, offering space for relaxation. Lush greenery and floral elements enhance the natural environment, with a barn-like structure visible in the background.
Home in Keene
4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars2 months ago
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
Guest favorite
A well-maintained outdoor pool area features a clear blue water pool surrounded by lounge chairs and umbrellas. The pool deck is paved and includes both shaded and sunlit seating options, with greenery providing a natural backdrop.
Home in Jamaica
4.96 out of 5 average rating, 25 reviews

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars2 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!
Guest favorite
An aerial view captures a modern home surrounded by lush greenery. A tranquil in-ground pool is set within a landscaped area, complemented by a stone fire pit and a gazebo. The exterior features a variety of trees, enhancing the serene atmosphere.
Home in Dorset
4.95 out of 5 average rating, 22 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

StacyRating, 5 stars2 months ago
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!
Superhost
An outdoor pool area features a large swimming pool surrounded by spacious concrete decking. Several lounge chairs are arranged neatly along the perimeter. Adjacent to the pool, a children's play structure is visible, set against a backdrop of green trees.
Home in Wilmington
4.78 out of 5 average rating, 55 reviews

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

AdamRating, 5 stars2 months ago
Awesome property! Stayed here for a ski trip with friends, we had a great time and the house was a great size for all of us! Hot tub works great and the indoor fireplace was fun to use as well. Would absolutely stay again. Super polite and responsive hosts.

Condo rentals with a pool

Guest favorite
A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars1 month 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.
Guest favorite
A spacious dining area features a long wooden table that seats eight, complemented by modern light fixtures. Large windows allow natural light to fill the room, while a sliding glass door offers access to a private outdoor space. A console cabinet is visible against the wall.
Condo in Dover
5 out of 5 average rating, 14 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

AlexanderRating, 5 stars1 month ago
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.
Superhost
A private deck is shown, furnished with two blue chairs placed beside a wooden railing. The view includes a serene landscape of trees and patchy snow, indicative of the changing seasons.
Condo in Dover
4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Christoph GRating, 5 stars1 month 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
A well-maintained outdoor pool is surrounded by sun loungers, creating a serene atmosphere. Lush greenery and trees frame the background, providing a natural setting. The concrete deck features handrails for easy access, while clear skies above invite relaxation.
Condo in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars1 month ago
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.
Guest favorite
An indoor swimming pool features a tranquil blue water surface, surrounded by wooden paneling and high, sloped ceilings. Natural light floods in through multiple windows, while comfortable lounge chairs are positioned along the edges of the pool.
Condo in Dover
4.95 out of 5 average rating, 58 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

DavidRating, 5 stars3 weeks ago
Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!
Guest favorite
A welcoming entrance to Crown Point is depicted, featuring a large sign with bold lettering. The sign is framed by a wooden structure and surrounded by vibrant flowers in various colors, adding a touch of natural beauty to the landscape.
Condo in Stratton
4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

DrewRating, 5 stars1 month 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.
Top guest favorite
An outdoor heated pool is set within a well-maintained garden, surrounded by lounge chairs and shaded by umbrellas. Lush greenery frames the area, enhancing the inviting atmosphere of the resort. A charming building with multiple windows is visible in the background.
Condo in Ludlow
4.96 out of 5 average rating, 51 reviews

3 Bedroom Castle Town Home

TomRating, 5 stars1 month ago
For our family of three this home fit us perfectly. You CAN certainly have more guests but it truly fit our needs. The set up was VERY spacious and cozy at the same time. The women at the desk are so kind and very good at their jobs. Not only did we feel at home when we arrived to our place, meeting them made us feel even more welcome. The castle was exquisite and an amazing experience in itself. The quaint town of Ludlow is a heart beat away with everything you need. All and all we can't say enough about how satisfied we are with Andy's home, the pricing, the staff and location! Our experience was amazing, memorable and we will be returning for sure next year! We are planning to come with our best friends next year & their kids because of your amazing home & our fantastic experience! 😁 Thank you again for opening your home to our family! The Baers
Guest favorite
A cozy living area is highlighted by a stone fireplace, topped with a wooden mantle. A large television is mounted on one wall, while plush seating surrounds a wooden coffee table. Stacked firewood is neatly arranged beside the fireplace, adding to the warm ambiance.
Condo in Dover
5 out of 5 average rating, 23 reviews

Lyon Family Lodge - Ski-in/ski-out

BethRating, 5 stars4 months ago
Great location, ski on ski off and very nice community not far from restaurants. Jared was very responsive and flexible with check in time. Overall a great condo on the mountain and would stay here again.

Quick stats about vacation rentals with a pool in Wardsboro

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Wardsboro
  6. Rentals with pools