Vacation rentals with a pool in Stratton

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Top-rated rentals with a pool in Stratton

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A clear swimming pool is surrounded by lounge chairs and an umbrella. Nearby, picnic tables are situated on a grassy area, with trees visible in the background, providing a peaceful setting for relaxation.

Condo in Dover

4.91 out of 5 average rating, 113 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favorite

The outdoor area features a central swimming pool surrounded by landscaped gardens. Multiple lounge chairs are arranged along the poolside, with a hot tub located nearby. The view includes neighboring trees and the facade of the condo, all under a clear blue sky.

Condo in Stratton

4.97 out of 5 average rating, 171 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

Guest favorite

A serene outdoor area is featured, showcasing a private heated pool surrounded by a brick patio. Lush greenery defines the background, and a rustic wooden table with chairs sits nearby, providing a space for relaxation in nature.

Chalet in Winhall

4.89 out of 5 average rating, 114 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

Guest favorite

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

4.88 out of 5 average rating, 180 reviews

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

Top guest favorite

A swimming pool is surrounded by lush greenery, inviting relaxation and enjoyment. The clear blue water reflects the surrounding landscape, providing a refreshing appeal. A person is seen in the water, engaged with a floating device, highlighting the leisure activities available at the property.

Guesthouse in Granville

4.91 out of 5 average rating, 932 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Top guest favorite

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

4.99 out of 5 average rating, 250 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Guest favorite

A spacious living area features large windows that allow natural light to fill the room, highlighting a stone fireplace and wooden accents. A comfortable sofa is arranged near a coffee table, with a dining area visible in the background, creating a cozy gathering space.

Cabin in Wilmington

4.91 out of 5 average rating, 146 reviews

Chic Chalet | Hot Tub · Clubhouse · Mt. Snow

Escape to The Sugar Maple Chalet, your stylish family retreat in the heart of Wilmington, Vermont. This thoughtfully updated four-bedroom home blends cozy charm with modern comforts—think high-speed Wi-Fi, a private outdoor hot tub, and a fun-filled basement bar and game room. Just a few minutes from local shops, restaurants, ski slopes, and scenic hiking trails. One well-behaved pet is welcome to join the adventure! AC installed when temperatures average above 78 degrees.

Guest favorite

A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.

Cabin in Guilford

4.95 out of 5 average rating, 174 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Top guest favorite

A serene private pool is framed by natural stone, surrounded by lush greenery and a few lounge chairs. The inviting water reflects the sunlight, providing a tranquil space for relaxation. Umbrellas are positioned nearby for shade.

Barn in Newfane

4.98 out of 5 average rating, 161 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

Guest favorite

The outdoor pool area features a large swimming pool with clear blue water, surrounded by lounge chairs. Green trees line the perimeter, creating a serene backdrop. A building with large windows stands nearby, providing shelter and amenities for guests.

Condo in Dover

4.84 out of 5 average rating, 127 reviews

Walk to Mt. Snow-Spa-Summer Pool

*Amenity rich studio only a 5 minute walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

Guest favorite

A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.

Guesthouse in Williamstown

4.92 out of 5 average rating, 249 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.

Top guest favorite

A spacious outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. Trees and greenery line the background, enhancing the natural setting. A building with large windows is visible nearby, contributing to the inviting atmosphere.

Condo in Dover

4.99 out of 5 average rating, 122 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.