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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Superhost

A spacious pool area is surrounded by lush greenery and autumn foliage. The inviting swimming pool reflects the clear sky, with lounge chairs placed around its perimeter. A charming house with a covered porch in the background adds to the serene setting.

Home in Roxbury

5 out of 5 average rating, 22 reviews

Zoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT

PoshPadsCT - 1-BR Large Open Pool House with Rec Room/Office/Sleeper Queen Sofa. Luxury Down Feather Beds, Comforters, Pillows, Frette Pressed Cotton Sheets, towels, Bathrobes. Roxbury and Washington are the best country escapes under 2 hours to NYC with the best homes, restaurants and activities. It is the country escape of choice to actors, writers, artists, Wall Street execs and more. A rural farm area of the best homes and estates in historic Litchfield County. Best country destination!

Top guest favorite

Home in Warren

5 out of 5 average rating, 48 reviews

Moody Pond House: Weekend Country Escape

Brand new family friendly modern home with in-ground gunite pool set on 18.5 acres with a large pond and adjacent to 150 acres of protected land. 5 minute drive from Lake Waramaug, a 2 minute drive from Hopkins Vineyard and 15 minutes from The Mayflower Hotel. Situated conveniently between the historic towns of New Preston and Kent this home provides everything you need for a relaxing stay including fully stocked kitchen, outdoor dining table, gas grill, fire pit, hiking on property & much more.

Superhost

An outdoor swimming pool is surrounded by a stone patio, featuring lounge chairs for relaxation. In the background, a rustic wooden bungalow complements the natural setting, with trees displaying vibrant autumn hues, creating a serene environment for outdoor enjoyment.

Bungalow in Morris

4.94 out of 5 average rating, 65 reviews

Cozy Pool House, Hot Tub, Gym, Treehouse Game Barn

Magical bungalow retreat with pool, cedar sauna, steam shower, game barn, gym and three story treehouse in bucolic country setting. Surrounded by protected lands great for hiking and tons of summer and winter activities including Bantam Lake, Mt. Tom skiing and snowboarding, and endless White Memorial Foundation trails. This is a private pool house located on a small compound. Absolute privacy with your own parking, entrance, heating system, and very secluded setting at the back of the property.

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

4.85 out of 5 average rating, 108 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.

Guest favorite

A serene outdoor pool area is surrounded by lush greenery and mature trees. Several lounge chairs are positioned around the pool, along with a dining set. A stone patio borders the pool, creating a spacious area for relaxation and enjoyment of the natural scenery.

Apartment in Kent

4.93 out of 5 average rating, 147 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Guest favorite

A serene outdoor area features a sparkling blue pool surrounded by lush greenery. A charming gazebo stands nearby, offering shaded seating. A decorative lion statue is positioned in the foreground, adding an elegant touch to the tranquil scene.

Home in New Milford

4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

Pool is closed for winter September 15-May 15th thank you Take it easy and relax at our unique and comfy getaway! With amazing outdoor spaces, plus pool and spa hot tub! Across the street is the lovely town reservoir. Close by are Lovers Leap State Park, Candlewood Lake, and amazing antiquing including New Englands largest flea market, Elephants Trunk! Wonderful farmers markets, and the quaint town of New Milford is also a short drive, has great shops, restaurants, and a cute movie theater.

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

4.9 out of 5 average rating, 49 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

20% off JULY/AUG MONTHLY- 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 by the firepit w/loved ones. Pool deck area in rear of house is closed, under maintenance work until 5/26/25

Top guest favorite

A view from the deck reveals a landscaped yard surrounded by trees, featuring an in-ground pool. Two lounge chairs are positioned near the water's edge, while flower beds add color to the lush greenery. Sunlight filters through the foliage, creating a serene atmosphere.

Home in Roxbury

5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

Mid-Century Modern, newly renovated 3 bedroom, 2.5 bath located on a secluded road. Inground heated pool & mature landscaping. Enjoy Sonos inside and out. Light shines into the living room, vaulted ceiling, wall of windows and sliders to a wooden deck overlooking the pool. Dining room with floor-to-ceiling windows and skylights. 2 bedrooms and 2 full baths on the main level; a 3rd bedroom with balcony, and a half bath. Electric charging station. Pool is currently close for the season.

Top guest favorite

The outdoor area features a tranquil private pool set against a backdrop of lush greenery and autumn foliage. A wooden fence encloses the space, with expansive views of rolling hills and trees, creating a serene and inviting atmosphere.

Home in Warren

4.96 out of 5 average rating, 28 reviews

Farm Valley Cottage + 60 ft Pool

Country getaway, light filled 3-bedroom cottage, private 60' pool with sweeping farm valley views, plus standalone guest studio. Nestled on 7 acres of nature, where a flock of chickens welcome you with fresh eggs every morning. Enjoy the pool, BBQ, fire pit, apple orchard, pond, outdoor shower and screened porch overlooking distant mountain ridge views. Warren is in rural Litchfield County, within a 2-hour drive from NYC.

Guest favorite

A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.

Home in New Milford

4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

THIS IS A PRIVATE HOME🏡 THE BOTTOM FLR 2 car garage and a double bedroom with a full bathroom attached. THE MIDDLE FLR KITCHEN, LIVING, DINING 1/2 bath, wrap-around decks w/ a fire pit THE TOP FLR 1 K rm w/ a fireplace & a private deck 1 Q rm 1 ba w/ jet tub & standing shower 6 acres Foothills of the Berkshires May-Sept We provide day passes for access to tennis, pickle ball, pool, yoga, swim, water aerobics

Top guest favorite

A private pool is surrounded by a natural stone wall, with lush greenery and trees in the background. Chaise lounges are positioned near the water's edge, providing a serene space for relaxation. The pool reflects the clear sky, enhancing the calm atmosphere of the estate.

Guesthouse in Cornwall

5 out of 5 average rating, 38 reviews

Charming Guest Cottage with Private Pool

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 spa behind 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.

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, 84 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.