
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.

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.

Sweet Updated 1B Condo on Access Road- Powderhound
Close to everything! We're located at the base of Sugarbush Access Road - Catch the resort shuttle right out your door! Across the street from the Mad River if you want to take a dip or catch a fish. Across the parking lot from Decor Restaurant & Bar. Down the road from SB Golf course. Super close to mountain bike trails & bike shuttle. Warren offers TONS of great hiking, biking, swim holes, etc. Our place is recently updated. Clean & Cozy. Murphy bed. Pullout couch & chair. Remodeled bath.

Cozy Ski in/Ski out 2 Bedroom at Sugarbush!
The owner of this property is severely allergic to dogs. It is a serious health risk. If you travel with a service dog we request you please book one of our other great properties. This condo offers the perfect slopeside location, steps from the "Out to Lunch" ski trail. Spend winter days exploring world-class skiing or snowshoeing through scenic trails, then return in the summer to relax by the pool or adventure along miles of hiking and biking paths. The ideal spot for your Sugarbush escape!

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

Stowe 3BR Townhouse-Excellent location & amenities
Our townhouse is located just off the Mountain Road, between the picturesque village of Stowe and Mount Mansfield. On site amenities include indoor & outdoor pool, hot tub, sauna, tennis courts and game room. XC and alpine skiing, hiking, mt. biking, golf, and many cultural events are at your fingertips. We are just 200 yds. from the Bike Path, on the bus route to the Mountain, and within walking distance to fabulous restaurants. Come and enjoy the many special events Stowe has to offer.

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/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.

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.

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.

Butternut at Sugarbush
Tucked into a quiet wooded setting just minutes from Sugarbush and Mad River Glen, this charming two-bedroom, two-bath condo at Butternut Hill is the perfect retreat for couples or families looking to enjoy Vermont in every season. Whether you’re here for a romantic ski getaway, a peaceful hiking weekend, or a fun family adventure, this warm and welcoming home offers just the right mix of comfort, privacy, and location.
Popular amenities for Waitsfield rentals with a pool
House rentals with a pool

Vintage Tollhouse Double Ski in/out Townhouse

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

Winter Wonderful Waitsfield Spacious VT Home w/Spa

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Stoweaway

The Vista: 12 min to Stowe, Pool, Theater, Hot Tub

Ski-In from Slopes | Sugarbush Home w/ Fireplace
Apartment rentals with a pool

Stowe 1 BR at Topnotch Resort Next to Heated Pool

Lovely 3-BR Stonybrook Townhouse With Mtn Views

Cozy Condo- Sleeps 6 - Central Stowe Location!

Ski-In Ski-Out Toll House Lift

The Bridges Resort - Near Lincoln Peak Base

The Cozy Condo at Smuggs Resort!

SlopeSide Escape: Ski In/Out

Cozy Little Mountain Condo
Other holiday rentals with a pool

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

Cozy, Comfy & Sunny Renovated Sugarbush Condo

Ski-In Ski-Out Toll House Lift - The Lodges

Mountainside Condo at Sugarbush, Vt

Village View at Spruce Peak

Welcoming 2BR Mountainview | Deck | Pool

The Snow'd Inn!

Sunny One Bedroom Ski On/Off Condo-Warren, VT
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 € 96 per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Waitsfield holiday rentals include wifi 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!
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- Rentals with pools United States
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Dartmouth College
- University of Vermont
- Stowe Mountain Resort
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Middlebury College
- Shelburne Museum
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Warren Falls
- Waterfront Park
- Camp Plymouth State Park
- Lake Champlain Chocolates
- Snow Farm Vineyard & Winery
- Kingdom Trails
- Elmore State Park
- Quechee Gorge
- Fairbanks Museum & Planetarium
- Cold Hollow Cider Mill




