Vacation rentals with a pool in Chittenden County

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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 favorite

Three modern condo units are visible, each featuring large windows and sloped roofs. Snow blankets the ground and rooftops, while wooden walkways lead up to the entrances. Surrounding trees create a natural backdrop, enhancing the feeling of seclusion.

Condo in Waitsfield

4.94 out of 5 average rating, 31 reviews

Family & Couples Valley Getaway

Location, comfort & charm! Our condo is the perfect escape from everyday life with its cozy treehouse feel and central location to the Mad River Valley's finest outdoor attractions and dining. 2 bedrooms, 1 loft with a full size bed, & 2 full baths comfortably sleeps six adults or a mix of adults + kids. 15 minutes from Sugarbush & Mad River Glen for world-class skiing & just 7 minutes to downtown Waitsfield. Scenic waterfalls steps from the condo, fully stocked kitchen, enjoy it all & unplug!

Superhost

A modern interior features a spacious living area with comfortable seating and a dining table. A well-equipped kitchen is visible, alongside a cozy sleeping area. Large windows allow natural light to brighten the space, with neutral tones creating a welcoming ambiance.

Camper/RV in Colchester

4.91 out of 5 average rating, 34 reviews

RV Camping by the Lake in Colchester, Vermont!

Enjoy Camping in Malletts Bay in a modern 2022 Keystone Hideout Bunk House! Features: *Master Bedroom with Queen Size Bed *4 other sleeping areas *Inside and Outside Shower *Built in Stereo with Speakers inside and out *PRIVATE WI-FI and new Roku Smart TV *Central Air, Heat and Vac *20' x 10' Deck with outdoor seating *Full inside kitchen and outside grill *Firepit *Inground pool in campground *Coin Op Laundry in campground *Public beach across the street *Bar/Restaurant across the street

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, 191 reviews

Cozy two-bedroom cabin near Smugglers Notch

Our two-bedroom log cabins (we have several) are a long-time family and small group favorite. Equipped with one queen bed, two twin beds (that can be converted to a king), one bath, a kitchen, living space, a woodstove or traditional fireplace, TV, and free WiFi, these cabins are cozy, yet spacious enough for the whole family or two couples to enjoy. This cabin has a maximum occupancy of 6 adults/children. Close to skiing/snowboarding, hiking, horseback riding, wedding barns and more.

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.

Superhost

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, 151 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 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, 6 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 wooden deck surrounds a spacious swimming pool, framed by lush greenery. Lounge chairs are arranged nearby, and colorful floatation devices are seen in the pool. A potted plant adds a touch of greenery to the deck, enhancing the serene outdoor space.

Apartment in Burlington

4.88 out of 5 average rating, 659 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!

Top guest favorite

Home in Waitsfield

5 out of 5 average rating, 31 reviews

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.

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 great day trips to the Mad River Valley & Stowe. Visit local breweries & wineries, farms & apple orchards, hikes and Lake Champlain.

Top guest favorite

A swimming pool is situated among lush greenery, featuring a wooden deck with a ladder leading into the clear blue water. Surrounding trees and manicured grass create a serene outdoor environment.

Guest suite in Jericho

4.97 out of 5 average rating, 150 reviews

Serenity Now! 30 min from Burlington or Stowe!

This space is attached to main home, however has its own private entrance. With beautiful views of Mount Mansfield right outside your door. We have some walking paths on and close to our property. Mount Mansfield is minutes away and Burlington & Stowe only 30 minutes. Jericho also offer shopping for all ages near by. Dining and grocery within minutes also helps for a relaxing time away.

Superhost

An outdoor pool is surrounded by freshly fallen snow, with a white fence outlining the area. Snow-covered trees and a distant mountain create a serene backdrop. The building features multiple stories and balconies, providing a view of the winter landscape.

Condo in Cambridge

5 out of 5 average rating, 3 reviews

2 Bedroom 2 Bath Smugglers Notch Resort

Two Bedroom two bath deluxe condo at Smugglers Notch Resort. Voted #1 family resort destination in America. Enjoy the skiing, sledding, multiple pools, water slide parks (in summer), hot tubs, kids indoor recreation center, rock climbing, restaurants, freshwater lake (Summer) & kids baby sitting. note: All pictures of rooms & kitchen may differ depending on unit Wyndahm assigns you.

Guest favorite

A multi-story condo building is visible, nestled among lush green mountains. The surrounding area features a gravel parking lot with several vehicles. The sky is partly cloudy, contributing to a serene outdoor environment.

Condo in Richmond

4.92 out of 5 average rating, 37 reviews

Family condo ski in/ski out Bolton main lodge!

Family-friendly condo in the main lodge at Bolton Valley Resort! Set up for any combination of kids and adults to come and explore all that BV has to offer. Condo is in the lodge building with 2 restaurants, ski/bike shop, rentals. Up the hill from the fitness center with indoor pool, hot tub, arcade, golf simulator, bar, and new outdoor pool too!