
Vacation rentals with a pool in Chittenden County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chittenden County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Mott House, South Hero Vermont
Apple Island Resort offers a variety of accommodations. The Lewis & Laura Mott House is rich in history & overlooks Apple Island Marina. The L&L Mott House is both the oldest & newest accommodation offered. Remodeled in 2018 with exquisite attention to detail, the historic house gives the architectural feel of an 1830s farmhouse while offering the latest in modern conveniences. Able to accommodate up to 8 guests, the L&L Mott House will provide an unparalleled home base for your special day.

North Burl - 1BR Loft with Private Porch
Private entrance 1 bedroom apartment in safe quiet burlington neighborhood. Master BR has 1 queen bed, closet, and work table. Living room has 1 twin daybed that pulls out to king size bed. Sofa, dining table, work table, TV and closet. Full kitchen including stovetop, oven, microwave, fridge, etc. 1 bathroom with shower. Large private porch with seating. (Hammock w/ stand available) Off-street parking for 2 cars, convenient to bus line, bike path, lake and river trails. Parks nearby.

Romantic one-bedroom cabin near Smugglers Notch
Our one-bedroom log cabins (we have several) have everything you need for a private, romantic getaway for two. With a king-sized bed, woodstove, two-person whirlpool tub, kitchen, bath, living room, TV, and free WiFi, these cabins have all the comforts of home and serve as a peaceful escape from everyday stress. This cabin has a maximum occupancy of 4 guests, with a sleeper sofa in the living area. Close to skiing/snowboarding, snowmobiling, hiking, horseback riding, wedding barns and more.

Cozy Little Mountain Condo
Relax on the mountain in our little condo. A cozy space to enjoy fresh mountain air. Enjoy easy access for ski in/out, hiking, mountain biking, leaf peeping…something to love here during every season! Bedroom with a queen bed. Pull out couch is best suited for children or one adult—two large adults may find it a tight fit. Located approximately half-way between Burlington and Stowe, about 30 minute drive to either/or. Or check out Waterbury (our favorite) about 15 minutes away!

Ski, Hike & Bike Basecamp Condo
Relax with the whole family at this peaceful condo tucked into the trees with easy access to all that the Mad River Valley has to offer. It is a 10 min drive to just about everything: Sugarbush, Mad River Glen, Blueberry Lake, mountain biking, leaf peeping, waterfalls, swimming, fishing, and great eats! Plus some hiking, snowshoe and mountain bike trials right outside the door. Depending on the season, snuggle up by the stove, try out the sauna, play tennis or relax by the pool.

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.

2-bedroom Condo at Bolton Valley
A spacious 2-bedroom condo for the entire family at Vermont's most family-friendly ski resort! This condo is located within Bolton Valley Resort, next to the sports center and a short walk to the ski lifts. Enjoy year-round adventures! Alpine, Nordic, and backcountry skiing, as well as mountain biking, hiking, swimming (indoors and out) and an indoor skate park. Enjoy all the mountain vistas--winter, spring, summer and fall--and find adventure around every bend!

Lakeside Bungalow ~ Pool | Hot Tub | Beach
Welcome to this Lakeside Retreat. This cozy waterfront property offers stunning lake views and access to a private beach. Enjoy a fully equipped kitchen, a spacious living area, and an outdoor deck for relaxing and watching the sunsets. Perfect for a family getaway or romantic escape. This property is a short drive to downtown Burlington for shopping and dining. Unwind in the hot tub, cool down in the pool or simply soak in the natural beauty of Malletts Bay!

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!

Winter Wonderful Waitsfield Spacious VT Home w/Spa
The ideal home for a memorable vacation in Waitsfield, Vermont offers over 3,000 sq ft of well-appointed living space. Only 15 minutes from Sugarbush & Mad River Glen and 1.4 miles from Waitsfield center, this house is perfectly situated for fun in any season. With a new and modern hot tub, fire pit, screened porch, gym, gargage with EV charger, ping pong & more, you'll never be bored! Sleeps 6 guests comfortably in 3 spacious bedrooms.
Popular amenities for Chittenden County rentals with a pool
House rentals with a pool

Mansfield Manor at Essex

4-bedroom Vermont Farmhouse close to Smuggs'

7-bedroom house close to Smugglers Notch

3BR lake home with hot tub, pool, & in-home gym

Vermont Guest House: Family-Friendly, EV, Dogs

Ski condo at Sugarbush

Sanctuary on the Brook

Winter in Spacious Waitsfield Home w/Spa & Loft
Condo rentals with a pool

Lovely riverfront condo near MRG/Sugarbush

Smuggler's Notch Vermont/ 1 bedroom Deluxe

Smugglers Notch 3 Bedroom

Bolton main lodge family condo ski in/ski out!

Skier's Paradise Mad River/ Sugarbush

Wyndham Smugglers' Notch | 2BR/2BA King Bed Suite

Family friendly slope side condo w/ free parking.

SlopeSide Escape: Ski In/Out
Other vacation rentals with a pool

Ridgeview Cabin near Smuggler's Notch

Field & Stream Dream Cabin near Smugglers Notch

Guest House on Otter Creek!

Cozy two-bedroom cabin near Smugglers Notch

Smugglers Notch Resort 2 Bedroom

1br Deluxe Unit -Nature Escape- Smugglers' Notch

Modern Cabin near Burlington VT

Smuggler's Notch Resort in Vermont 1br suite, Frid
Destinations to explore
- Rentals with breakfast Chittenden County
- Townhouse rentals Chittenden County
- Rentals with lake access Chittenden County
- Family-friendly rentals Chittenden County
- Beachfront rentals Chittenden County
- Rentals with a hot tub Chittenden County
- Tiny house rentals Chittenden County
- Guesthouse rentals Chittenden County
- Rentals with an EV charger Chittenden County
- Rentals with a fireplace Chittenden County
- House rentals Chittenden County
- Rentals with outdoor seating Chittenden County
- Farmstay rentals Chittenden County
- Ski-in/ski-out rentals Chittenden County
- Rentals with a washer and dryer Chittenden County
- Private suite rentals Chittenden County
- Smoking-friendly rentals Chittenden County
- Fitness-friendly rentals Chittenden County
- Chalet rentals Chittenden County
- Waterfront rentals Chittenden County
- Condo rentals Chittenden County
- Bed and breakfasts Chittenden County
- Rentals with a kayak Chittenden County
- Boutique hotel rentals Chittenden County
- Rentals with a patio Chittenden County
- Rentals with beach access Chittenden County
- Apartment rentals Chittenden County
- Pet-friendly rentals Chittenden County
- Rentals with a fire pit Chittenden County
- Rentals with pools Vermont
- Rentals with pools United States
- Sugarbush Resort
- Jay Peak Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Jay Peak Resort Golf Course
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Pump House Indoor Waterpark
- Northeast Slopes Ski Tow
- Cozy Cottages & Otter Valley Winery
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Burlington Country Club
- Country Club of Vermont
- Val Caudalies - Vignoble & Cidrerie
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Domaine du Ridge
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- Montview Vineyard