
Vacation rentals with a pool in Waitsfield
Find and book unique homes with a pool on Airbnb
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 G$27,187 GYD per night before taxes and fees

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Over 390 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!
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

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

Cozy VT Getaway, Heated Pool, Sleeps 4
The Notchbrook Nook is nestled at the top of Notchbrook road in a group of condos that overlook beautiful views and is only minutes from Stowe Mountain Resort. The pool is open for summer months until Labor Day & reopens in late November for ski season. The Matterhorn restaurant sits at the bottom of the road and is a must experience Aprés spot. You are literally less than 10 mins from the slopes & downtown restaurants/shops. The condo and Notchbrook property are NON-smoking.

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!

Bridges Cozy Condo Hideaway at Sugarbush
Imagine: après-ski, you're curled up by the gentle glow of your gas fireplace, or unwinding in a spa-inspired bathroom with radiant heated floors and a dual-head rain shower. Key Amenities & Details: 🛌 Queen Bed | Sleeps 2 🧖 Heated Bathroom Floors & High-Tech Bidet Toilet ☕ Nespresso Machine & Gas Grill 🔥 Gas Fireplace & Private Washer/Dryer 🏊 Shared Pool, Sauna, Fitness Center 🚫 Please Note: No Pets/Smoking. Hot Tub closed until Dec 1, 2025.

Concrete Ski House Near Sugarbush
2 Minutes from Sugarbush, Lincoln Peak. Architect Dave Sellers’ “Archie Bunker” is a high-concept concrete manse filled with vintage artifacts. Winner of 2010 American Institute of Architects Award. Includes a private spring-fed swimming pool and golf green for putting and chipping. For a video tour, search "Archie Bunker Offbeat Spaces". Please be sure to read Other Details to Note PRIOR TO BOOKING. THIS IS AN UNUSUAL HOUSE AND ISN'T FOR EVERYONE.

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

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.

Bridges #90. 3 Bedroom/2 bath with many amenities.
Welcome to Unit 90 at The Bridges! This our family ski condo, please enjoy yourselves and the amenities the Bridges has to offer. The kitchen is fully equipped with your basic needs as well as a crockpot, blender, and electric griddle! In the club house is an indoor pool, hot tub, sauna, workout room, game room, and tennis courts. In the summer, outdoor pools and tennis courts are available as well.
Popular amenities for Waitsfield rentals with a pool
House rentals with a pool

Mountain View Farmhouse w/ Orchard, Pool is Open!

Sylvan Hideaway - Pool - Game Room - Firepit

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

Peak Waitsfield VT Spacious Home w/Pool & Spa

Modern, Trendy Townhome in Stowe! Newly Remodeled

Charming Barre Getaway

Stoweaway

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

3rd Floor Studio @ The Lodge at Spruce Peak

NEW 2025 Sugarbush Bridges Resort Outpost

The Bridges Resort - Amazing location

Lovely 3-BR Stonybrook Townhouse With Mtn Views

Convenient Mad River/Sugarbush Condo with WIFI

Simple 1B condo at the foot of Sugarbush Access Rd

Ski-In/Ski-Out / 1 bed / Seasonal Pool

Stylish Ski Condo with Pools, Hot Tub, and Gym
Other vacation rentals with a pool

Renovated condo 3 miles from Mtn. (unit #32)

Bridges condo at Sugarbush

Modern Condo • Walk to Lifts!

3+ bedroom ski in/out Townhouse with views

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

The Snow'd Inn!

*Seasonal Rental* Beautiful Condo 3 NearSugarbush

Treetops & sun; hot tub, pool & tennis; 1 BR condo
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- Sugarbush Resort
- Pico Mountain Ski Resort
- Dartmouth College
- Bolton Valley Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- Killington Resort
- University of Vermont
- Middlebury College
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Kingdom Trails
- Snow Farm Vineyard & Winery
- Camp Plymouth State Park
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Elmore State Park
- Quechee Gorge
- Waterfront Park
- Boyden Valley Winery & Spirits
- Dartmouth Skiway





