Vacation rentals with a pool in Winhall

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Popular amenities for Winhall 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!
Guest favorite
The indoor pool area features a serene blue water surface, bordered by natural stone and wooden paneling. A gently sloping ramp leads into the water, while lounge chairs line the adjacent wall, providing a comfortable spot for relaxation. The space is illuminated softly, creating a calm environment.
Home in Wilmington
5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars3 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!
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.
Top guest favorite
An aerial view showcases the expansive landscape of the estate, featuring two ponds surrounded by lush greenery and trees. The serene fishing pond reflects the clear sky, with rolling hills visible in the background, inviting guests to explore the natural beauty of the surroundings.
Home in Dover
5 out of 5 average rating, 58 reviews

The Villa - Industrial Farmhouse with Hot Tub

StephanieRating, 5 stars3 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
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 swimming pool is surrounded by lounge chairs and umbrellas, providing ample space for relaxation. Lush greenery and trees line the background, contributing to a serene atmosphere. The sky is bright with scattered clouds, enhancing the inviting outdoor setting.
Home in Manchester
4.89 out of 5 average rating, 9 reviews

Your country home awaits! Pool, tennis, Dogs loved

RichardRating, 5 stars26 months ago
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

Guest favorite
A spacious outdoor pool area is surrounded by manicured grass. Lounge chairs are positioned around the pool, providing space for relaxation. The building features large windows and multiple decks, blending modern architecture with a natural setting.
Condo in Killington
4.96 out of 5 average rating, 130 reviews

Dog-Friendly Mountainside Escape/Pool/AC

ShaneRating, 5 stars6 days ago
Beautiful condo, nice location near the Sunrise lift and Bear Mountain. Very home like atmosphere in condo.
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
Aerial view captures the snow-covered landscape surrounding the ski slopes, with well-defined runs visible against the mountainside. A tranquil lake reflects the scene, bordered by trees. Nearby buildings, including the condo complex and community amenities, are discernible in the setting.
Condo in Dover
4.89 out of 5 average rating, 9 reviews

New - walk to Mt Snow w/ Tub & Gym

ToniRating, 5 stars1 month 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!
Guest favorite
A spacious living area is presented, featuring a comfortable brown sofa adorned with decorative pillows. Two side tables with lamps provide soft lighting. Large doors open to a view outside, allowing natural light to brighten the room, which is complemented by soothing green walls.
Condo in Stratton
4.95 out of 5 average rating, 19 reviews

Stratton Duplex Condo Steps to Lifts, Village!

NathalieRating, 5 stars4 weeks ago
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.
Guest favorite
The exterior of the building is framed by flowering plants and greenery, creating a welcoming entrance. A wooden pathway leads to the front door, flanked by manicured landscaping and decorative rocks. Large windows illuminate the interior, allowing for natural light.
Condo in Dover
4.96 out of 5 average rating, 24 reviews

Mt. Snow Condo with Pool-Hot Tubs-Sauna MTN Views

Axuan VrolijkRating, 5 stars3 weeks ago
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

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