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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.

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Guest suite in Jericho

4.74 out of 5 average rating, 280 reviews

Apartment, comfy and cozy with kitchen + hot tub

Cozy one bedroom apartment with private entrance. EXTRA SPECIAL - schedule a Seasonal ( February and March) offering of traditional Vermont Sugar on Snow Desert Party on one of your day/ evening stays! One hour gathering in main house kitchen . $10/person extra charge ! Your private apartment has Own kitchen and bath, romantic gas fireplace, wireless internet, large screen tv with cable. Lovely rural setting seasonal flower gardens and open lawn. Hot tub, year round with perfect star gazing.

Guest suite in Starksboro

4.96 out of 5 average rating, 52 reviews

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.

Condo in Richmond

4.73 out of 5 average rating, 83 reviews

Family friendly slope side condo w/ free parking.

This ski-in/out trailside condo is located less than 30 miles from the best dining/shopping/hiking in Stowe, Burlington, Waterbury & Montpelier. It includes free parking & WiFi. Located next to the Mountain Market & James Moore Tavern, this gem is just a few steps away from swimming or skateboarding at the Sports Center, as well as 5 out of the 6 resort's ski lifts, including Wilderness which provides access to all natural backcountry alpine terrain & the Vista Quad's mountain bike trail system.

Rental unit in Bolton Valley

5 out of 5 average rating, 56 reviews

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 at the resort in the winter. Hiking and playing disc golf in the spring/summer/fall. Mountain biking with lift service in the summer/fall. There is something to love here during every season! Located approximately half-way between Burlington and Stowe, about 30 minute drive to either. Or check out the little town of Waterbury (our favorite) about 15 minutes away- towards Stowe.

Home in Essex

4.98 out of 5 average rating, 52 reviews

Game Room, Fireplace, Garage in Quiet Neighborhood

Our whole house rental includes 3 bedrooms and two baths. Garage bay available - walk right into the kitchen - for your convenience. Game room in basement with Pool Table and other games. Fireplace (gas/inside). Deck firetable. Air conditioning in each bedroom (end of May-end of Sep). Neighborhood pool available Mem Day - Mid-Sept - about a 2 min drive from our rental. ($30/group/whole stay). Central to Vermont's 4 season enjoyment - Lake Champlain, Mt. Mansfield, Skiing, Biking, Shopping.

Home in South Hero

4.97 out of 5 average rating, 32 reviews

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.

Chalet in Bolton Valley

4.94 out of 5 average rating, 71 reviews

Swanky Mountain Chalet 30 min.s from Burlington

Beautiful mountain chalet just steps away from Bolton Valley Resort and Mountain Bike Park in Bolton, Vermont. Best backcountry access in the state for hiking and a new Gravity Logic mt bike park! All the amenities, two private bedrooms with 2 full baths, amazing spot on the ski (and bike) trails, and just 30 minutes from Burlington and the airport. Sports center with indoor tennis and pickleball, indoor and outdoor pools, hot tub, sauna within walking distance, and great food and bars.

Cabin in Cambridge

4.93 out of 5 average rating, 399 reviews

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.

Rental unit in Burlington

4.88 out of 5 average rating, 617 reviews

PvtBeach Lake-Cabin HotTub WalkBikeDine Breweries!

⛱️ 🍺🍕🎣🏊‍♀️Private beach guesthouse (beach 3 blocks away), hot tub (open all year), 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 in Colchester

5 out of 5 average rating, 6 reviews

Lakeside Bungalow~pool hot tub

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!

Rental unit in Richmond

4.93 out of 5 average rating, 134 reviews

Mountain Getaway for Couples at Bolton Valley

Bright and charming studio at Bolton Valley Resort. Ski, ride, 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 in Essex Junction

5 out of 5 average rating, 10 reviews

Mansfield Manor at Essex

Mansfield Manor, the perfect place to relax and enjoy Vermont to the fullest. Located in the heart of Chittenden County, close to many amenities including Lake Champlain, Stowe Resort and Smugglers Notch. Your home away from home, in a rural setting within 5 minutes of the Essex Experience and 30 minutes to Church St Marketplace in Downtown Burlington. Enjoy our breweries, local restaurants, and genuine Vermont Maple products.

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Popular amenities for Chittenden County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Cambridge

4.91 out of 5 average rating, 43 reviews

4-bedroom Vermont Farmhouse close to Smuggs'

Home in Cambridge

4.88 out of 5 average rating, 25 reviews

7-bedroom house close to Smugglers Notch

Home in Cambridge

5 out of 5 average rating, 7 reviews

Cozy Smuggs Townhouse Getaway

Home in Waitsfield

5 out of 5 average rating, 30 reviews

Autumn in Waitsfield VT Spacious Home w/Spa

Home in Lincoln

5 out of 5 average rating, 13 reviews

Vermont Guest House: Family-Friendly, EV, Dogs

Home in Waitsfield

4.93 out of 5 average rating, 58 reviews

Spacious Summer Home in Waitsfield w/Spa & Loft

Home in Winooski

4.92 out of 5 average rating, 12 reviews

'House of Art' Group Escape By Parks & Lake!

Condo rentals with a pool

Condo in Bolton Valley

4.91 out of 5 average rating, 35 reviews

2-bedroom Condo at Bolton Valley

Condo in Waitsfield

4.95 out of 5 average rating, 22 reviews

Family & Couples Valley Getaway

Condo in Richmond

5 out of 5 average rating, 24 reviews

Family condo ski in/ski out Bolton main lodge!

Condo in Waitsfield

4.96 out of 5 average rating, 23 reviews

Ski, Hike & Bike Basecamp Condo

Condo in Cambridge

4.86 out of 5 average rating, 14 reviews

Wyndham Smugglers' Notch | 1BR/1BA King Bed Suite

Condo in Waitsfield

4.5 out of 5 average rating, 6 reviews

Mountain Magic: Walk to Mt. Ellen Slopes in 5 Min

Destinations to explore