Vacation rentals with a pool in Litchfield County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Litchfield County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 183 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Guest favorite

A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.

Guesthouse in Southbury

4.93 out of 5 average rating, 330 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Superhost

A spacious outdoor deck features a large dining table surrounded by several chairs, with an umbrella providing shade. A swimming pool is visible in the background, complemented by well-maintained grass and trees lining the property.

Villa in Morris

4.88 out of 5 average rating, 124 reviews

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Guest favorite

A clear blue pool is surrounded by a stone patio, featuring colorful floatation devices in the water. A diving board extends over the edge, while lounge seating and cabana beds are visible in the background. The pool area is enclosed by a white fence.

Apartment in Burlington

4.86 out of 5 average rating, 113 reviews

Charming apartment with breathtaking view!

The guest apartment ( FULLY RENOVATED FINISHED BASEMENT) is an addition to our luxurious home. A 2 bedroom apartment with one king sized bed, Queen sized bed and a plush leather pull out sofa. Pool l table. Large in ground pool, 2 cabana beds, fire pit and dining table. Pool and gated backyard is exclusive to guests. We include netflix, hulu and hbo max. THE (HEATED) POOL IS OPENED IN MAY AND CLOSED LATE SEPTEMBER. The pool is cleaned daily in the morning. The pool is exclusive to guests.

Superhost

A newly renovated kitchen features modern cabinetry complemented by a wood beam overhead. Checkerboard flooring adds visual interest, while stylish bar stools provide seating at the island. Ample counter space and sleek appliances create a functional cooking area with natural light filtering through the window.

Home in Litchfield

4.69 out of 5 average rating, 26 reviews

Litchfield Modern Farmhouse

This newly renovated farmhouse is complete with a gorgeous kitchen, new bathrooms and spacious bedrooms. A perfect spacious and serene space. Enjoy the pool and wrap around porch during the warmer months or drive through the scenic towns to see the gorgeous fall foliage, experience fall festivals, apple picking, or to catch a glimpse of some of the spots that inspired Gilmore Girls there is plenty to do and see! In the winter months come home after a day of skiing to this cozy space.

Top guest favorite

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

4.96 out of 5 average rating, 358 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite

A spacious outdoor pool area is outlined by a brick patio, featuring a clear blue swimming pool and shaded seating under a pergola. Lush greenery surrounds the space, while a large building and trees are visible in the background, contributing to a serene atmosphere.

Barn in Bloomfield

4.98 out of 5 average rating, 123 reviews

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Guest favorite

Apartment in Brookfield

4.92 out of 5 average rating, 284 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Top guest favorite

The exterior of a rustic wooden building is visible, surrounded by greenery and a fenced area. A pool area is situated in front, with the sky showcasing dramatic clouds. Sunlight highlights the warm tones of the wood and the landscaped garden.

Farm stay in Canaan

4.97 out of 5 average rating, 90 reviews

A luxurious farm hideaway in the treetops

Want to get away to your own private hideaway, overlooking rolling hills and a pastoral farm? The space is small but luxurious, with a well-equipped kitchen, a comfortable bed with high-end 100% cotton linens, lots of soft throw blankets, real leather furnishings, and a marble-tiled bathroom. The views from the deck are stunning. Plenty of hiking spots, fine dining, and cultural sites nearby. Or just lounge by the pool (Memorial Day through Labor Day)

Top guest favorite

A private pool is framed by a natural stone wall, with several lounge chairs placed around its edges. Lush greenery and trees surround the area, while a clear blue sky adds to the serene atmosphere. The pool area invites relaxation and leisure.

Guesthouse in Cornwall

5 out of 5 average rating, 44 reviews

Charming Guest Cottage with Private Pool & Hot Tub

Nestled in a narrow valley in Litchfield County, this charming guest cottage is located on a stunning 275 acre estate at the end of a mile long private drive. With its own private pool and hot tub nestled within stone walls, it is perfect for couples looking for a romantic retreat. Rural, but not remote, we are a 2+ mile walk to the village of Cornwall, and a 25 minute drive to Litchfield, Kent, Sharon, and Falls Village.

Top guest favorite

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

Home in Litchfield

4.99 out of 5 average rating, 88 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Nestled just outside the center of Bantam, this immaculate 3 bedroom 2.5 bath home with a pool is the ultimate retreat. The home is perfectly located for enjoying the area's top attractions, like lake activities, skiing at Mohawk, hiking the trails of White Memorial, Litchfield's Village Green where you can enjoy fine dinning, shopping and visit historic sites. Pool is open and heated May 15th to Sept 15th.

Superhost

A serene swimming pool is visible in a sunlit pool deck area surrounded by lush greenery. Multiple lounge chairs are positioned around the deck, inviting relaxation. A kayak rests alongside the pool, adding a hint of outdoor adventure.

Home in Litchfield

4.89 out of 5 average rating, 55 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

Leave your worries at the front door of this New England gateway. An open, airy interior may make you feel like staying at home reading all day long, but there's so much to explore nearby. Head out to Black Rock State Park for a scenic hike through lush forests, followed by a leisurely afternoon sampling wines at local vineyards. Gather at this stylish home and outdoor by the firepit w/loved ones.