Become a host

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.

%{current} / %{total}1 / 1
Guest favorite
A spacious home stands blanketed in fresh snow, showcasing a classic design with a gabled roof and multiple dormer windows. The surrounding landscape features tall trees, creating a serene winter scene. A welcoming front porch with a railing is visible, inviting guests inside.
Home in Waitsfield
4.93 out of 5 average rating, 61 reviews

Winter in Spacious Waitsfield Home w/Spa & Loft

Our ideal home for a memorable vacation in Waitsfield, Vermont. This location offers over 3,900 sq ft of well-appointed living space. Only 15 min from Sugarbush and Mad River Glen ski resorts and 1.4 miles from Waitsfield center. This house is perfectly situated for fun in every season. Equipped with a new and modern hot tub, fire pit, screened porch, gym, ping pong, so you'll never be bored! Plenty of room with space to sleep up to 8 guests comfortably in 3 spacious bedrooms. We love it here!

Top guest favorite
A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.
Guest suite in Starksboro
4.94 out of 5 average rating, 110 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.

Superhost
A spacious living area features a large red sectional sofa positioned near two windows, offering mountain views. A small wooden coffee table with a chess set sits on a patterned rug. A floor lamp and side tables add functional touches to the room.
Condo in Richmond
4.74 out of 5 average rating, 103 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.

Guest favorite
A quaint two-story house is set against a backdrop of lush greenery. The exterior is painted in a soft green hue, complemented by white railings and a spacious front porch. The surrounding landscape features tall grass and a clear sky, enhancing its serene appeal.
Home in South Hero
4.98 out of 5 average rating, 44 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.

Guest favorite
The living room features a light blue sofa complemented by a patterned wall hanging. A small wooden coffee table rests in front, with a television mounted on the wall. Natural light enters through sliding glass doors that lead to a private outdoor area.
Apartment in Burlington
4.86 out of 5 average rating, 14 reviews

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.

Guest favorite
A warm and inviting living area features natural wood paneling, a cozy seating arrangement with plush sofas, and a TV mounted on the wall. A woodstove provides warmth, while a coffee table displays snacks and drinks. Light streams through window treatments with soft curtains.
Cabin in Cambridge
4.93 out of 5 average rating, 402 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.

Top guest favorite
A modest front deck is visible, featuring railings and a few steps leading to an entrance door. A potted plant hangs above, while vibrant flowers are located below, set against a backdrop of trees displaying autumn foliage.
Condo in Bolton Valley
5 out of 5 average rating, 82 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, 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!

Top guest favorite
A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.
Apartment in Monkton
4.98 out of 5 average rating, 128 reviews

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.

Guest favorite
A spacious studio features a king size bed with crisp white linens and a cozy sitting area. A large window provides natural light and scenic views. Artwork adorns the walls, and a stylish chaise lounger complements the wood flooring.
Apartment in Bolton Valley
4.93 out of 5 average rating, 159 reviews

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.

Top guest favorite
A warm and inviting living area includes a striped couch and two upholstered armchairs. A wooden coffee table sits in the center, enhanced by a small potted plant. A gas fireplace is framed by a wooden feature wall, and a television is mounted above.
Condo in Bolton Valley
4.94 out of 5 average rating, 47 reviews

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!

Guest favorite
Home in Colchester
4.96 out of 5 average rating, 28 reviews

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!

Superhost
A serene lakeshore scene is captured at sunset, with the sun dipping below the waterline, casting warm light over the tranquil surface. Silhouettes of trees line the shore, their reflections mirrored in the gentle waves, creating a peaceful ambiance.
Apartment in Burlington
4.88 out of 5 average rating, 704 reviews

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!

Popular amenities for Chittenden County rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favorite
A two-story house is set against a backdrop of rolling mountains and an expansive sky. The exterior features a mix of gray siding and white trim, with a welcoming front porch. A driveway leads up to the garage, surrounded by open green space.
Home in Essex Junction
4.94 out of 5 average rating, 18 reviews

Mansfield Manor at Essex

Guest favorite
A spacious living area features comfortable grey sofas with decorative cushions, arranged around a wooden coffee table. A rustic brick fireplace adds warmth, and large windows provide ample natural light while offering views of the surrounding greenery. Wooden beams frame the ceiling.
Home in Cambridge
4.91 out of 5 average rating, 46 reviews

4-bedroom Vermont Farmhouse close to Smuggs'

Guest favorite
The exterior of the Mansfield House is displayed, showcasing a welcoming wooden facade with a sloped roof. Colorful flower beds with blooming plants frame the entrance, which features a covered porch supported by red pillars.
Home in Cambridge
4.88 out of 5 average rating, 26 reviews

7-bedroom house close to Smugglers Notch

Top guest favorite
The exterior of a two-story home is captured under a clear blue sky, showcasing a fresh layer of snow covering the roof and front yard. Trees line the background, providing a serene and private setting.
Home in Waitsfield
5 out of 5 average rating, 39 reviews

Winter Wonderful Waitsfield Spacious VT Home w/Spa

A multi-story home is surrounded by trees and greenery, presenting a blend of stone and siding on the exterior. Large windows invite natural light, while a spacious yard features a mix of grass and fallen leaves.
Home in Colchester
4.63 out of 5 average rating, 19 reviews

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

Guest favorite
A spacious front porch offers a view of the vibrant autumn landscape, featuring trees in shades of orange and yellow. The porch is edged with wooden railings, and a wooden staircase leads down to a lush green pathway.
Home in Lincoln
4.94 out of 5 average rating, 18 reviews

Vermont Guest House: Family-Friendly, EV, Dogs

Superhost
A cozy living area is depicted, featuring two brown reclining sofas adorned with decorative pillows. A circular coffee table is centered, displaying a bottle of red wine, glasses, and a decorative fan. Exposed wooden beams add character to the space, complemented by warm lighting.
Home in Cambridge

Mountain View Modern Farmhouse

Home in Waitsfield
4.5 out of 5 average rating, 8 reviews

Sanctuary on the Brook

Condo rentals with a pool

The kitchen features wooden cabinetry and a spacious island with a dark stone countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A dining area with wooden chairs and a table is situated nearby, complemented by soft, ambient lighting.
Condo in Waitsfield
4.7 out of 5 average rating, 20 reviews

Lovely riverfront condo near MRG/Sugarbush

Superhost
Condo in Cambridge

Smuggler's Notch Vermont/ 1 bedroom Deluxe

Superhost
A comfortable living area features a cozy sofa and armchairs with plaid upholstery. A wooden coffee table displays books and magazines. A television is housed within a wooden console, while a stone fireplace adds warmth to the space. Large windows provide natural light and a view of surrounding greenery.
Condo in Cambridge

Smugglers Notch 3 Bedroom

Guest favorite
A two-story condo is set amidst snow-covered ground and trees. The building features large windows and a covered entrance with steps leading up to it. The exterior is painted in a light color, contrasting with the surrounding winter landscape.
Condo in Waitsfield
4.94 out of 5 average rating, 31 reviews

Ski, Hike & Bike Basecamp Condo

The exterior of a multi-story building is framed by lush greenery and well-maintained landscaping. A winding pathway leads to the entrance, flanked by vibrant plants and trees, offering a welcoming appearance in a sunny setting.
Condo in Cambridge
4.82 out of 5 average rating, 17 reviews

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

Superhost
A well-maintained building is surrounded by snow, featuring multiple units with balconies. A ski lift is seen in the foreground, transporting guests while others enjoy skiing on the gentle slope nearby. Bright blue skies provide a clear contrast to the winter scene.
Condo in Cambridge

1br Deluxe Unit -Nature Escape- Smugglers' Notch

Superhost
Condo in Waitsfield

Skier's Paradise Mad River/ Sugarbush

Superhost
A snow-covered ski lift ascends through trees blanketed in fresh snow. The clear blue sky contrasts with the white landscape while ski tracks lead up the slope, indicating a popular route for winter sports enthusiasts.
Condo in Cambridge
5 out of 5 average rating, 3 reviews

Smugglers Notch, Vermont - 1Bd Dlx

Other vacation rentals with a pool

Guesthouse in Vergennes
New place to stay

Guest House on Otter Creek!

Guest favorite
A warm living area is highlighted by natural wood paneling and a cozy woodstove. A coffee table is set with fresh fruit and drinks. A softly lit lamp beside a comfortable chair adds to the inviting atmosphere, while a door leads to a bedroom.
Cabin in Jeffersonville
4.93 out of 5 average rating, 192 reviews

Cozy two-bedroom cabin near Smugglers Notch

A multi-story building is situated against a backdrop of snow-covered mountains. The structure features multiple windows and balconies, revealing a light-colored exterior. Snow blankets the ground, while pine trees are visible in the foreground, contributing to the winter scenery.
Condo in Cambridge

Smuggler's Notch Resort in Vermont 1br suite, Sund

A winter scene depicts a multi-level building surrounded by snow-covered ground and evergreen trees. Majestic mountains rise in the background, with clear blue skies above, creating a serene alpine atmosphere.
Apartment in Cambridge

Smugglers Notch Resort 2 Bedroom

A modern log cabin features natural wood siding and large windows, allowing ample light. A welcoming entrance is highlighted by a wooden front door framed with a decorative archway, leading to a small set of stairs surrounded by trees.
Cabin in Colchester

Modern Cabin near Burlington VT

Guest favorite
A cozy studio cabin is highlighted by warm wooden walls and rustic decor. A queen-sized bed is positioned next to a small table set for two, featuring simple dishware. A fridge and kitchen area are visible, along with an inviting lounge chair near the window.
Cabin in Cambridge
4.97 out of 5 average rating, 195 reviews

Studio Cabin near Smugglers Notch

The living area is furnished with a teal couch and a single armchair, positioned beside a coffee table. A dining table with two chairs is visible, along with a flat-screen television. Large windows provide natural light and access to the outdoor view.
Apartment in Richmond

Mountainside Studio at Bolton Valley

A spacious kitchen features modern stainless steel appliances set against soft yellow cabinetry. A large granite island offers seating for four, while a wooden dining table accommodates six. Natural light streams through the window, illuminating the inviting space.
Apartment in Cambridge

Top Ski and Summer Resort Luxe

Destinations to explore