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.

0 of 0 items showing

1 of 3 pages

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

4.95 out of 5 average rating, 82 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

4.75 out of 5 average rating, 93 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

4.97 out of 5 average rating, 34 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

A clear blue swimming pool is set within a fenced area, with several lounge chairs arranged along the poolside. A rustic building is visible in the background, surrounded by green trees and open fields, under a light cloud cover.

Cabin in Cambridge

4.97 out of 5 average rating, 195 reviews

Studio Cabin near Smugglers Notch

Our studio log cabins (we have several) are cozy and quaint, making them the perfect choice for the couple looking for a private getaway or for the lone traveler looking to disconnect from the hustle and bustle of everyday life. This cabin has a max occupancy of two guests. Equipped with a queen-sized bed, gas log stove, kitchen, bath, couch, TV, and free WiFi, a studio cabin provides our guests with a safe space to relax and unwind. Close to all spring, summer, fall, and winter activities.

Guest favorite

The image captures a vibrant orange chalet nestled among lush greenery. Large windows reflect sunlight, and wooden steps lead up to a welcoming entrance. A grassy area features stepping stones, enhancing the natural surroundings of this inviting mountain retreat.

Chalet in Bolton Valley

4.95 out of 5 average rating, 79 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.

Guest favorite

An outdoor pool area is surrounded by wooden decking, showcasing lounge chairs arranged neatly on either side. The inviting pool features clear water, with a simple building visible in the background amidst lush green trees.

Condo in Waitsfield

4.97 out of 5 average rating, 29 reviews

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.

Top guest favorite

A refreshing inground pool reflects the clear sky, bordered by a stone patio. The backyard features vibrant gardens alongside a two-story home with a combination of light gray and red siding. A deck area can be seen on the left side of the house.

Apartment in Monkton

4.99 out of 5 average rating, 119 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, 153 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.

Guest favorite

A small black cabin is set on a grassy area surrounded by trees. A fenced-in space is visible, along with a satellite dish mounted on the structure. Two chairs are positioned outside, offering a space to relax and enjoy the natural surroundings.

Tiny home in Ferrisburgh

4.81 out of 5 average rating, 32 reviews

Dog-Friendly Secluded Cabin

Small cabin on our 24 acre country site. One charming room with a connecting dressing room and full bath. Fresh water pond for swimming plus a clay tennis court. Dogs are welcome due to the fencing we have installed around the small meadow that surrounds the cabin. A limit of two dogs per visit. AVAILABLE FROM MAY 15th TO OCTOBER 15TH. We also have a private king-bedded suite off the main house which rents for $150/night. A small child could sleep on the futon couch.

Top guest favorite

The exterior of a two-story condo building is presented, featuring gray wooden siding and large windows. Colorful flowers and lush greenery are visible in the foreground, with a ramp leading to the entrance. A lamppost stands nearby, adding to the welcoming outdoor space.

Condo in Bolton Valley

4.93 out of 5 average rating, 45 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

A waterfront property is showcased with a spacious deck featuring seating and a hot tub. The private beach area is visible alongside the sandy shoreline. Nearby, a grassy area is bordered by trees, enhancing the natural setting. Multiple homes can be seen along the shoreline.

Home in Colchester

5 out of 5 average rating, 10 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!

Guest favorite

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, 678 reviews

Lake Cabin Pvt-Beach, Hot Tub Walk-Dine Breweries!

⛱️ 🍺🍕🎣🏊‍♀️ 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!