
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.

Epic Views of the Green Mountains
Luxurious bohemian style overlooking one of the most epic views in the Green Mountains. Surrounded by 25,000 acres of National Forest and complete seclusion, yet just a short ride from several towns. Spacious, immaculate, modern home with rustic beams and gorgeous wood floors. Each of the three bedrooms (and baths!) have a wonderful view. The master bedroom is massive and has sweeping views out over the Battell Wilderness and the Long Trail. The front of the cottage is a wall of windows overlooking a beautiful pond and the Green Mountain National Forest. No light pollution. No noise except for the tree frogs and the sound of the White River rushing over the rocks far below in the hollow. It's worth mentioning that Breadloaf Mountain Cottage was a gift that I am grateful for. I still can't believe that I am so lucky to be able to enjoy it frequently. Please understand that those sweeping, epic views you see all around you when you are there, come at a price. Being perched atop a mountain in the wilderness has obvious benefits, but due to frequently changing weather, access and utilties are sometimes a bit more tricky than something in town. Please be prepared to be patient with the weather and the WIFI. While my internet is as good as anywhere in Vermont, it is a rural network and is likely more quirky than urban or suburban utilities. I have a 20mbps service. Breadloaf Mountain Cottage is at the top of a ridge that runs parallel to scenic Route 100. It sits at about 1600 feet above sea level. While completely secluded, it is just 1.3 mile to the Granville Store, and just a few minutes more to Hancock, Rochester and Warren. You could spend weeks just exploring the hiking, biking, swimming and fishing opportunities right from the property! Breadloaf Mountain Cottage is located on Forest Road 55, just off scenic Route 100. While it is easily accessible year round, a 4X4 or AWD vehicle is highly recommended in snow and mud. Quality AT or snow rated tires are a must in the winter. This is true generally in Vermont. Come prepared.

Mountain View Farmhouse w/ Orchard White Christmas
This magical property is Vermont at its finest. Bring the whole family to this idyllic farmhouse with panoramic mountain views, large private pool, apple orchard, flower gardens, fire pit and much more. Be as free as you imagine on 14 private acres of lawn, perennial gardens, fruit trees and lush woods with a meandering stream. Let the kids swim in the pool all day while you read in the shade of old locust trees while taking in one of the best views in Vermont.Find us on insta: @upper_east_eden

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.

Cozy/Private, close to hospital, i-89
Relax in Central Vermont. Easy access to hike/ski/tour Private apartment, sleeps up to 5, peaceful area, beautiful views, close to VAST trails 5 minutes from I-89, 15 minutes to Norwich University, 50 minutes to burlington, 45 minutes to ski areas, 5 minutes to Rock of Ages, 10 min to Central VT Hosp. Private entrance/bath/living space, deck overlooking trees/mtns/sliding, microwave, mini fridge, grill, washer dryer, hot plate. Moments to restaurants. 1 queen, twin over full bunk.

Cozy VT Getaway, Heated Pool, 3mi Stowe Mtn, WiFi
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.

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.

Tiny House on Vermont Homestead
We are located in the hills of central VT, close to good hiking, skiing and swimming. Disconnect to reconnect. Our homestead is based on permaculture landscape design.Relax by the living pool, unwind in the traditional sauna, 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 and Upper Yurt on VT Homestead

Amazing location, views, shared hot tub in Stowe!
Come stay in Stowe at this beautiful 1000 sq foot, two bedroom, two bath condo centrally located within walking distance to many of Stowe's favorite hot spots. Stunning views of the Worcester Mountains from your walk out deck. Plenty of space to relax by the propane fire after a long day of skiing. The condo association includes an indoor pool and shared hot tub. This condo offers a King bedroom with ensuite and a Queen bedroom with a shared bathroom.

Safe Quiet Lake Cabin Pvt-Beach HotTub Pool Path
⛱️ 🍺🍕🎣🏊♀️ Private beach 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!

Home Run condo near Toll House base
Newly renovated 1 bedroom condo, Located at Toll House base area in the Original Lodge building near Stowe Mountain Resort. Ski-in/out access in the winter (weather dependent with a 5-min flat ski to the Toll House Lift). Swimming pool, tennis courts and hiking trails in the summer. This cozy one bedroom condo comes with a fully equipped kitchen, living room with gas fireplace, washer & dryer, and private ski storage outside of the 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.
Popular amenities for Waitsfield rentals with a pool
House rentals with a pool

Sylvan Hideaway - Lower Village - Fire Pit - Games

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

Theater room & close to mountain!

The Pinnacle Spa & Retreat

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Winter in Spacious Waitsfield Home w/Spa & Loft

EPIC Stowe Getaway - Great For Families & Friends

Design Build Concrete House Near Sugarbush
Apartment rentals with a pool

NEW 2025 Sugarbush Bridges Resort Outpost

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

2 bed, 2Bath, New AC, fireplace, amazing location!

Newly Renovated Condo, 1 Bedroom + Loft at Bridges

2BR Sugarbush Mountain Condo

NEW: Cozy, Mountainside Sugarbush Condo w/pool

The Cozy Condo at Smuggs Resort!

Slopeside: Mtn Views, ski in/out, 5 min to village
Other holiday rentals with a pool

Cozy, Comfy & Sunny renovated Sugarbush condo

Quiet Smuggs Retreat Ski in/out

Bridges condo at Sugarbush

3+ bedroom ski in/out Townhouse with views

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

Convenient Mad River/Sugarbush Condo with WIFI

Cozy Mountain Retreat in Stowe

Newly built luxe villa with mountain views & perks
Quick stats about holiday rentals with a pool in Waitsfield
Total rentals
10 properties
Nightly prices starting at
£82 before taxes and fees
Total number of reviews
350 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Jersey City Holiday rentals
- Capital District, New York Holiday rentals
- Pet-friendly rentals Waitsfield
- Rentals with outdoor seating Waitsfield
- Rentals with a hot tub Waitsfield
- Bed and breakfasts Waitsfield
- Rentals with an EV charger Waitsfield
- Rentals with a washing machine and dryer Waitsfield
- Family-friendly rentals Waitsfield
- Apartment rentals Waitsfield
- Rentals with breakfast Waitsfield
- House rentals Waitsfield
- Rentals with a firepit Waitsfield
- Rentals with a patio Waitsfield
- Waterfront rentals Waitsfield
- Rentals with a fireplace Waitsfield
- Rentals with pools Washington County
- Rentals with pools Vermont
- Rentals with pools United States
- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Burlington Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Storrs Hill Ski Area
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Boyden Valley Winery & Spirits
- The Quechee Club
- Snow Farm Vineyard & Winery
- Montview Vineyard