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Holiday rentals with a pool in Waitsfield

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Waitsfield

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

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Guest favourite
Home in Warren
4.83 out of 5 average rating, 131 reviews

Charming Sugarbush Standalone Condo

Situated on the mountain with a panoramic view, this stand alone condo - ski-on/ski-off (winter) / spectacular vistas (fall) / Mad River fun (summer) / blissful bloom (spring) - will be your home away from home. This spacious, three-floored home is filled with light and great for couples, families, business travelers, or solo adventurers. Friendly property manager, Constancia is able to greet guests and offer recommendations. Please find our cleaning protocol in "Other things to note" section.

Top Guest favourite
A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.
Guest suite in Starksboro
4.94 out of 5 average rating, 139 reviews

Private Suite in the Green Mountains

Relax in a country setting, centrally located to Vermont attractions. This private apartment in the trees boasts three beds and a full kitchen. With views of the Green Mountains, you will be a short drive away from quaint towns, skiing, breweries, hiking, and swimming. On the property, enjoy the fresh mountain air, changing leaves, and local flora and fauna. In summer, cool off after a hike or bike in the shared pool. In winter, you're 15 minutes to Mad River Glen and 30 to Sugarbush Ski Resort.

Guest favourite
A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.
Yurt in Randolph
4.94 out of 5 average rating, 468 reviews

Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT homestead and Tiny house on VT homestead

Top Guest favourite
A dining area is presented with a long wooden table, surrounded by several gray chairs. Two built-in benches with patterned cushions and pillows are positioned along the wall. A round mirror is mounted above the table, reflecting the space's natural light.
Townhouse in Stowe
4.98 out of 5 average rating, 162 reviews

Stowe, Newly Renovated Topnotch Resort Townhouse

Enjoy a top-notch experience at this newly renovated townhouse with free access to outdoor pools and hot tub and fire pit. Located 5 minutes from mountain! Take in all the amazing mountain air :)) For access to spa, indoor hot-tub with waterfall, indoor pool, steam, sauna, Fitness Center and shuttle to the ski resort a day rate of $78 fee is required (maximum of 6 people) additional guests may be added at $25 per day per guest. Also included is first come first serve activity court.

Top Guest favourite
A red-painted two-story house is framed by lush green grass and colorful flower beds. A welcoming porch features two white chairs and wooden barrels. A friendly dog is seated at the entrance, adding a homely touch to the exterior.
Place to stay in Johnson
4.99 out of 5 average rating, 175 reviews

Château Chavis

Indulge in a serene retreat at Chateau Chavis, a captivating and picturesque residence nestled on over ten acres of tranquil rural land in Johnson, Vermont. Conveniently situated just twenty minutes from Stowe and twenty-five minutes from Smugglers Notch, Chateau Chavis offers easy access to breathtaking waterfalls, scenic hiking trails, and the rail trail. Regardless of the season, this idyllic haven serves as an ideal destination for a staycation or a quintessential Vermont vacation.

Guest favourite
A spacious studio features a king size bed with crisp white linens and a cozy sitting area. A large window provides natural light and scenic views. Artwork adorns the walls, and a stylish chaise lounger complements the wood flooring.
Apartment in Bolton Valley
4.93 out of 5 average rating, 176 reviews

Cozy Bolton Valley Ski Studio • Hike & Relax

Cozy ski lodge studio at Bolton Valley Resort, set at 2,000 feet and surrounded by over 5,000 acres of Green Mountain wilderness. Direct trail access makes it easy to ski, snowboard, snowshoe, bike, or hike scenic trails, then return to a warm, quiet mountain retreat. Inside you'll find a king bed, full kitchen, TV, and bathtub—perfect for relaxing after a day outdoors. Ideal for couples or solo travelers seeking a peaceful mountain escape. Note: Not suitable for pets or children.

Top Guest favourite
Snow-covered grounds are visible, framed by tall evergreen trees. In the background, a mountain slope is partially visible, marked by ski trails. A white fence and signs of winter's chill set the scene, with cloudy skies overhead.
Condo in Warren
4.97 out of 5 average rating, 140 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Enjoy all the MRV has to offer in our renovated 2 Bedroom, 1 bath condo at the Bridges Resort. The Resort features two outdoor pools, one indoor pool, hot tub, indoor and outdoor clay and Har-Tru tennis and Pickleball courts, updated fitness center, volleyball, basketball, horseshoes, badminton and children's playground. Tennis lessons and clinics available on site. Both gas and charcoal grills are available. Two Fire pits located just outside outdoor. Plenty of convenient parking.

Top Guest favourite
The modern kitchen features a farmhouse table with six white chairs and a long bench, accommodating group dining. Stainless steel appliances are visible alongside dark cabinetry. Large windows provide natural light, highlighting the sleek aesthetic and open layout connecting to the living space.
Townhouse in Stowe
4.94 out of 5 average rating, 156 reviews

Ski In Ski Out, Chic, Fun, Cozy, Grt Location!

Ideal location! Ski/bike/hike right from our front door, and also minutes to the best of Stowe restaurants, craft breweries, shopping, trails & swimming holes. We like staying in stylish boutique hotels, so we decorated our country home to feel like one. 3 bedrooms each on own level, two baths, spotless, stylish, foosball, strong Wi-Fi and cozy fireplace conversation pit - so nice for playing boardgames and watching movies. We welcome you to enjoy our home and the magic of Stowe!

Top Guest favourite
A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.
Apartment in Monkton
4.98 out of 5 average rating, 130 reviews

Spacious Private Apartment w/ Green Mountain Views

Guests enjoy views of Camel's Hump & the Green Mountains and beautiful farmland to the East. This space is great for couples & solo adventurers. My home was built in 1810 & the Guest Studio was added onto the house in 1980. Conveniently located midway between Middlebury & Burlington, also a great home-base to take a day trip to the Stowe & the Mad River Valley. Much to explore- visit local farms & apple orchards, great hikes and Lake Champlain, breweries and wineries.

Guest favourite
A seasonal outdoor pool is surrounded by a fenced area, featuring lounge chairs and a colorful hammock. Lush green trees provide shade, while sunlight reflects off the clear water. A nearby cottage is visible in the background, adding to the tranquil setting.
Cottage in Stowe
4.77 out of 5 average rating, 265 reviews

Cute Cottage - Poolside - Minutes To Activities

Our cute little cottage has just been fully renovated. Open concept living space with 2 bedroom plus full size futon & 2 bathrooms & laundry. It is located within beautiful multi-acre property with seasonal pool. Ideal for 2 couples or a family. The fireplace is cozy in the winter and the covered porch with swing is great for appreciating the mountain views in the summer. Location couldn’t be better - minutes from slopes, trails and restaurants.

Guest favourite
A cozy living area is highlighted by a flat-screen TV displaying Netflix, positioned above a minimalist fireplace. A tabletop showcases two glasses of red wine beside a wooden platter of assorted cheeses and fruit, complemented by flowers in a vase and flickering candles.
Condo in Warren
4.88 out of 5 average rating, 215 reviews

Ski In/Ski Out with upgrades!

Newly renovated with comfort in mind! Brand new Nectar hybrid Queen mattress in bedroom. Lazy boy sofa w/ queen pullout w/ memory foam topper. Large chair in living room w/ large screen TV,Netflix & other channels. Well stocked kitchen, Wifi,books,movies & board games. Bedroom has tv. Located in Sugarbush Village, many restaurants, & activities,within walking distance. First floor unit with easy access.

Top Guest favourite
The dining area features a circular white table surrounded by four modern white chairs with wooden legs. Two black-and-white framed photographs adorn the walls alongside a decorative letter 'VT', adding character to the neutral-toned space.
Condo in Warren
4.98 out of 5 average rating, 140 reviews

NEW: Stylish Ski On/Ski Off Mountainside Retreat

- Newly constructed ski-on/ski-off condo - Incredible views of the mountain trails and woods - Well-appointed condo features fireplace, high-quality kitchen tools and premium bedding Convenience, location & style come together in this chic one-bedroom brimming with amenities. Ideal for couples or families, the condo is the perfect destination for all your Sugarbush and VT adventures.

Popular amenities for Waitsfield rentals with a pool

Quick stats about holiday rentals with a pool in Waitsfield

  • Total holiday rentals

    Explore 10 holiday rentals in Waitsfield

  • Nightly prices starting at

    Waitsfield holiday rentals start at $204 NZD per night before taxes and fees

  • Verified guest reviews

    Over 380 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Waitsfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Waitsfield rentals

  • 4.9 Average rating

    Waitsfield stays are highly rated by guests—averaging 4.9 out of 5!