
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

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.

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.

Upper Yurt Stay on VT 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 two listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT and Tiny house on VT homestead

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, fridge, grill, washer dryer, hot plate. Moments to restaurants. 1 queen, twin over full bunk.

Modest Mountain Dacha
Comfortable one bedroom , 450 sf condo ,small pullman kitchen, small balcony. • King bed in Bedroom, Living-room- 2 couches Powderhound complex includes: Pool open in summer season. And the Mad River just across the road 1000 feet for swimming, kayaking and tubing •Hostel Tevere Pub: light meals, hosts local bands. •on site bus stop: in season to ski areas & village. Sugarbush 3 mi., Mad River Glen 8, Long Trail, Catamount Trail :8 miles, Warren village-1

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.

Slopeside Bolton Valley Studio
Bright and charming studio at Bolton Valley Resort. Ski, ride, snowshoe, bike, hike within seconds of leaving your front door. The studio is at 2000' elevation tucked into the valley with easy access to dozens of beautiful trails. You'll experience nature at its best! When you're finished playing outside come inside to your home away from home. It has a king size bed, full kitchen, TV, and bathtub. Ideal for couples and solo travelers. Not suitable for animals or children.

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.

Bunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool
Escape and relax in dog friendly, cozy, quiet, 12x12, unique, furnished efficiency cabin with an 8x8 Hot Springs Grandee Hot Tub, an after skiing spa to wind down in after a lovely day enjoying VT's winter wonderland. Can sleep a family of 3, but roomier for a couple Less than one mile to Sugarbush parking lot at the base of the mountain

Sugarbush Mountainside Retreat - Ski in Ski out
Cozy and conveniently situated in the heart of Sugarbush Village, this recently renovated condo is a top floor end unit with views of the green mountains from every room. Regardless of the season you plan on visiting, this space is a perfect home base for all the Mad River Valley has to offer.
Popular amenities for Waitsfield rentals with a pool
House rentals with a pool

Sunset Treehouse

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

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Charming Sugarbush Standalone Condo

Gorgeous mtn forest retreat 3 mins from ski resort

Winter in Spacious Waitsfield Home w/Spa & Loft

EPIC Stowe Getaway - Great For Families & Friends

Design Build Concrete House Near Sugarbush
Condo rentals with a pool

3rd Floor Studio @ The Lodge at Spruce Peak

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

Lovely 3-BR Stonybrook Townhouse With Mtn Views

Newly Renovated Condo, 1 Bedroom + Loft at Bridges

NEW: Cozy, Mountainside Sugarbush Condo w/pool

Ski-In Ski-Out Toll House Lift

HomeRun Lodge:ski in/out, Mtn Views, hiking/biking

Amazing location, views, shared hot tub in Stowe!
Other holiday rentals with a pool

Cozy, Comfy & Sunny renovated Sugarbush condo

Year Round Green Mountain Escape- Bridges Resort

3+ bedroom ski in/out Townhouse with views

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

The Snow'd Inn!

Convenient Mad River/Sugarbush Condo with WIFI

The Bridges Resort - Near Lincoln Peak Base

Newly built luxe villa with mountain views & perks
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 $188 NZD per night before taxes and fees

Verified guest reviews
Over 350 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, Wi-Fi 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
- 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
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Rentals with a fireplace Waitsfield
- Family-friendly rentals Waitsfield
- Rentals with breakfast Waitsfield
- Rentals with an EV charger Waitsfield
- Rentals with a washing machine and dryer Waitsfield
- Rentals with a patio Waitsfield
- Condo rentals Waitsfield
- Bed and breakfasts Waitsfield
- Waterfront rentals Waitsfield
- Pet-friendly rentals Waitsfield
- House rentals Waitsfield
- Rentals with a hot tub Waitsfield
- Rentals with a fire pit Waitsfield
- Rentals with outdoor seating Waitsfield
- Rentals with pools Washington County
- Rentals with pools Vermont
- Rentals with pools United States
- Sugarbush Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Dartmouth Skiway
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Montshire Museum of Science
- Storrs Hill Ski Area
- Burlington Country Club
- Ethan Allen Homestead Museum
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- The Quechee Club
- Montview Vineyard
- Coolidge State Park




