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Vacation rentals with a pool in Litchfield

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Litchfield

  • Total vacation rentals

    Explore 20 vacation rentals in Litchfield

  • Nightly prices starting at

    Litchfield vacation rentals start at €60 per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Litchfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Litchfield rentals

  • 4.9 Average rating

    Litchfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Litchfield

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

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Superhost
A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.
Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

4.88 out of 5 average rating, 129 reviews
Top guest favorite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

4.96 out of 5 average rating, 395 reviews
Guest favorite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

4.96 out of 5 average rating, 145 reviews
Top guest favorite
The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.
Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

4.98 out of 5 average rating, 176 reviews
Top guest favorite
A spacious deck is set with comfortable seating arranged around a central fire pit, glowing softly as the sun sets. Trees frame the serene lake view in the background, enhancing the tranquil outdoor setting, complemented by softly lit lanterns.
Home in Goshen

Litchfield Hills Lakefront Getaway!

YellowBird welcomes guests with luxury vaca vibes + gorgeous water and sunset views on friendly Woodridge Lake, just minutes from Litchfield County’s charming small towns, golf, hikes + ski resorts. -2 hrs NYC, 2.5 hrs Boston, only 10 min from Litchfield village center -Gorgeous & fun all year -Enjoy 150 ft of lakefront, swimming, fishing, parks, golf, hiking, mountain and countryside vistas, foliage, covered bridges, antiquing, vineyards, top restaurants, cultural activities & skiing

5.0 out of 5 average rating, 86 reviews
Top guest favorite
A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.
Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter. Columbia County STR Registration #: COP-2025-015

5.0 out of 5 average rating, 111 reviews
Top guest favorite
A spacious living area features a brick fireplace at its center, surrounded by comfortable seating options. Light tones from the walls and furniture create a welcoming atmosphere. Large windows provide views of the outdoors, and a natural fiber rug adds texture to the floor.
Home in Litchfield

Litchfield Luxury Home w/Heated Pool

Escape to this fully renovated 4BR, 2.5BA estate on 12 private acres with sweeping views of Litchfield’s hills. Enjoy a heated pool (seasonal @ $50 per day upcharge), private gym, and walking trails. Inside, relax in beautifully furnished spaces with hardwood floors and New England charm. Just 3 miles from downtown Litchfield’s shops, dining, and hiking. Whether you’re sipping coffee while watching the sunrise or relaxing at sunset by the pool, the views are breathtaking year-round.

5.0 out of 5 average rating, 26 reviews
Top guest favorite
A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.
Barn in Bloomfield

Farm Stay with Horses & Pool | Mountaintop Views

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.

4.97 out of 5 average rating, 139 reviews
Top guest favorite
Guesthouse in Cornwall

The Pool Cottage at Narrow Valley Estate

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, or individuals looking to rest and regroup from too much work. It is a 2+ miles to the village of Cornwall, and a 25 minute drive to Litchfield, Kent, Sharon, and Falls Village.

5.0 out of 5 average rating, 74 reviews
Top guest favorite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

5.0 out of 5 average rating, 187 reviews
Top guest favorite
A charming two-story home showcases a blend of gray siding and natural stone accents. The front porch features white rocking chairs under a welcoming overhang. Large windows provide ample natural light, surrounded by well-maintained landscaping and trees in the background.
Home in Goshen

Northwest Connecticut Vacation House in Goshen

Our cozy home welcoming guests with vacation vibes on a private, friendly Woodridge Lake, just minutes from Litchfield County's most charming small towns and ski resorts. Only 2 hours from NYC, 2.5 hours from Boston and 10 min from Litchfield village green. You'll discover the lake is exceptionally well-cared for and has a great energy but without the crowds since there is no public boat launch and no jet skis allowed.

5.0 out of 5 average rating, 18 reviews
Top guest favorite
A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.
Farm stay in Redding

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

4.98 out of 5 average rating, 102 reviews

Popular amenities for Litchfield rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.
Home in Town of Taghkanic

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

4.99 out of 5 average rating, 123 reviews
Guest favorite
The single-story home is surrounded by vibrant autumn foliage, with colorful trees framing the property. A spacious wooden deck extends from the house, providing outdoor seating. The lawn is expansive and well-maintained, inviting relaxation in the tranquil setting.
Home in Kent

Country retreat on 4 private acres

4.96 out of 5 average rating, 46 reviews
Guest favorite
A spacious kitchen features light-colored cabinetry and a large island with quartz countertops. Stainless steel appliances are neatly arranged, and a traditional chandelier hangs above. A decorative rug lies on the wooden floor, creating a welcoming atmosphere in the bright and airy space.
Home in Litchfield

Iconic Litchfield Home in Town Center

4.87 out of 5 average rating, 30 reviews
Superhost
The exterior of a classic colonial home features white siding and dark shutters. Vibrant pink rhododendron bushes surround the front porch, which is adorned with white railings. The building's peaked roof and multiple windows are visible under a clear blue sky.
Home in Litchfield

Historic Colonial/Pool/Walk to Town

4.78 out of 5 average rating, 32 reviews
Top guest favorite
A modern two-story ranch home is positioned on a landscaped yard, featuring a mix of greenery and well-maintained pathways. Large windows dominate the front façade, allowing ample natural light. Decorative outdoor lighting stands in the foreground, adding subtle illumination to the exterior.
Home in Clinton Corners

High Meadows | Modern Farmhouse, Pool, 13 acres

4.99 out of 5 average rating, 73 reviews
Guest favorite
A comfortable living area features a striped sofa adorned with patterned cushions, positioned beside a wooden coffee table. A vase of fresh flowers sits atop the table. Light filters through a large window with divided panes, illuminating the space and connecting to the kitchen area visible in the background.
Home in Sherman

Designers Historic Connecticut Home

5.0 out of 5 average rating, 21 reviews
Superhost
Home in Sherman

Hillside Oasis

4.74 out of 5 average rating, 27 reviews
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

Farm Valley Cottage + 60 ft Pool

4.98 out of 5 average rating, 45 reviews

Other vacation rentals with a pool

Top guest favorite
Barn in Roxbury

Classic Red Barn with game room and gym

4.94 out of 5 average rating, 63 reviews
Top guest favorite
A serene pool is surrounded by natural stone landscaping and lush greenery, creating a tranquil outdoor space. A charming cottage is visible in the background, nestled among trees and vibrant flowering plants. Soft lighting adorns the trees, enhancing the peaceful atmosphere.
Villa in Washington

Charming Country House with Pool, HotTub & Gardens

5.0 out of 5 average rating, 18 reviews
Top guest favorite
An aerial view showcases the expansive stone-paved backyard, featuring a large swimming pool surrounded by lounge chairs. Lush greenery borders the area, contributing to a serene outdoor atmosphere. The image captures the inviting space, perfect for relaxation and leisure.
Guest suite in Watertown

Hidden Serenity at TuKasa - Pool & Billiards

4.95 out of 5 average rating, 62 reviews
Top guest favorite
Guest suite in Farmington

The Cottage at Apple Hill

5.0 out of 5 average rating, 61 reviews
Top guest favorite
Cottage in Goshen

Bluestone Cottage | Historic Goshen Retreat

5.0 out of 5 average rating, 6 reviews
Top guest favorite
Barn in Dover Plains

Punto Pino Farm Stay

5.0 out of 5 average rating, 11 reviews
Top guest favorite
Guest suite in Cornwall

A Slice of Paradise II in Northwest CT

5.0 out of 5 average rating, 18 reviews
Guest favorite
A serene view of Candlewood Lake is captured at twilight, revealing a vibrant pink and purple sky reflected on the water's surface. Lush trees frame the scene, while a small dock and green kayak are visible on the water, enhancing the tranquil lakeside atmosphere.
Cottage in New Milford

BUNTING HOUSE : CANDLEWOOD LAKEFRONT! 3BR CHALET

4.92 out of 5 average rating, 66 reviews

When is the best time to visit Litchfield?

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