
Vacation 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.

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.

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.

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

Cozy Sugarbush condo (Ski in&Ski out!)
Our newly renovated condo has all that you need to unplug and relax, either for ski in and ski out, to enjoy summer at one of the many water holes or an adventurous mountain biking ride or the beautiful foliage during wedding season in Vermont. Perfectly situated, near restaurants, several walking distance like the renowned Chez Henri. Historic Warren is close by with one of our favorite restaurants and bars (Tracks) and of course Sugarbush base is walking distance (or ski “Out to Lunch” down)

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.

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.

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.

Powder Hound Condo
Cozy one bedroom condo in the Mad River Valley, Sugarbush Ski resort and Mad River Glen Ski nearby. Walking trails, shops, restaurants and breweries close by. Deco Bar and Restaurant on-site! Waterbury VT is only 30 minutes where you can find Prohibition Pig Brewery, Cabot Factory annex, Ben and Jerrys Ice Cream Factory and many other place to go. Stowe, VT is 45 minutes, Von Trapp family lodge and brewery, Stowe Cider (personal favorite), Alchemist Brewery and Stowe Ski Resort

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.

Bikepath Lake Cabin Hot Tub & Private Beach ~ UVM
⛱️ 🍺🍕🎣🏊♀️ Private beach Attached guesthouse (beach 3 blocks away), hot tub ), heated swimming pool (open May-early September), walk to fishing, boating, dog friendly beaches, public tennis, volleyball, bocce ball courts bike paths picnic areas,& a diverse selection of top-rated restaurants and breweries. Relax and make the most of the amenities! Self check-in, safe parking, easy access to the Colchester Causeway and all of Burlington . A perfect getaway!

Ski On Ski Off Welcoming Slope Side Condo
Experience the best of summer at Sugarbush from our slope-side condo with a heated pool and scenic mountain views. Located on the “Out to Lunch” trail, enjoy easy access to hiking and biking right outside your door. Just a 5-minute walk to the base lodge for summer events, dining, and activities. Explore nearby Warren Falls, play the renowned 18-hole golf course, or relax in the heart of Vermont’s Green Mountains. The perfect mountain getaway awaits!

Year Round Green Mountain Escape- Bridges Resort
This is a turn key condo with 2 bedrooms, 1 bathroom, and a sleeper sofa that comfortably sleeps 6, at the Bridges Tennis and Ski Resort. It has a fully equipped kitchen, washer/dryer and includes all linens and towels. The resort includes 3 pools, a hot tub, sauna, fitness center, game room and tennis courts. There is a free winter shuttle that picks you up and brings you to the base of Lincoln Peak (Sugarbush) Electronic keypad access to unit
Popular amenities for Waitsfield rentals with a pool
House rentals with a pool

Last Run Stowe: Pool, spacious, 5min to Village

Vermont Mountain Summer Retreat

Mountain View Farmhouse w/ Orchard, Pool is Open!

Private 5BR Mt. view, pool, new hot tub

Peak Waitsfield VT Spacious Home w/Pool & Spa

Zenbrook: Sauna + Firepit | Pool | Luxury Design

Stoweaway

3 Acre Forest Retreat | Hiking Trails Pool Firepit
Condo rentals with a pool

Stowe 1 BR at Topnotch Resort Next to Heated Pool

Bridges #90. 3 Bedroom/2 bath with many amenities.

The Bridges Resort - Amazing location

Cozy 2 bed, 2Bath, pool, amazing location!

Lovely 3-BR Stonybrook Townhouse With Mtn Views

Cute two bedroom condo close to Stowe Mountain

Cozy Little Mountain Condo at BV Ski Resort

Ski in/out Condo @ The Lodge at Spruce Peak
Other vacation rentals with a pool

On Mountain Condo

NEW 2025 Sugarbush Bridges Resort Outpost

3+ bedroom ski in/out Townhouse with views

Bridges 77 at Sugarbush

Stowe Cottage, Private 34 acres, Lake, 5 mins town

The Snow'd Inn!

Convenient Mad River/Sugarbush Condo with WIFI

Simple 1B condo at the foot of Sugarbush Access Rd
Quick stats about vacation rentals with a pool in Waitsfield

Total vacation rentals
Explore 10 vacation rentals in Waitsfield

Nightly prices starting at
Waitsfield vacation rentals start at ﺩ.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 380 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Waitsfield vacation 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!
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Québec City Vacation rentals
- Newark Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- Rentals with a fireplace Waitsfield
- Family-friendly rentals Waitsfield
- Condo rentals Waitsfield
- Pet-friendly rentals Waitsfield
- Rentals with breakfast Waitsfield
- Rentals with a fire pit Waitsfield
- Rentals with a patio Waitsfield
- Bed and breakfasts Waitsfield
- Rentals with a hot tub Waitsfield
- House rentals Waitsfield
- Rentals with outdoor seating Waitsfield
- Waterfront rentals Waitsfield
- Rentals with an EV charger Waitsfield
- Rentals with a washer and dryer Waitsfield
- Rentals with pools Washington County
- Rentals with pools Vermont
- Rentals with pools United States
- Sugarbush Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Killington Resort
- Dartmouth College
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Kingdom Trails
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- Warren Falls
- Shelburne Museum
- Camp Plymouth State Park
- Elmore State Park
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Waterfront Park
- Quechee Gorge
- Boyden Valley Winery & Spirits
- Cochran's Ski Area





