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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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

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

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

Relaxation is offered in all parts of our bright and comfortable home, sitting on 4 acres of mature gardens and woodlands. Try the screened porch for evening dining, morning coffee on the sunny deck or rest poolside in the secret garden. Gardens bursting full of color, paths winding along ancient stone walls and woods full of bird life make this a peaceful retreat. Near East Hamlet Preserve, Lake Waramaug beach and Kent restaurants and shopping. 25 mins to nearest train station into NYC.

4.96 out of 5 average rating, 46 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

This historic home, designed and decorated by a talented artist, features four bedrooms, two bathrooms, and a unique "Glamping" shed. The property boasts a heated Gunite lagoon pool, perfect for relaxing and entertaining. Guests can dine at a ten-person farm table under charming string lights, surrounded by Restoration Hardware teak furnishings. The outdoor lounge area on the stone patio offers a cozy retreat, complete with an old-fashioned wood and rope swing hanging from an Elm tree.

5.0 out of 5 average rating, 21 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

Guest favorite

A charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.

Bungalow in Easthampton

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

4.93 out of 5 average rating, 581 reviews

Top guest favorite

A tranquil view of a pond is presented from a shaded deck. A wooden table and two chairs, featuring blue and green cushions, overlook the calm water surrounded by lush trees. The sky is partly cloudy, reflecting softly on the surface of the pond.

Cottage in Kent

1 Bed Pond Cottage w/ pool/hot tub/sauna access

Adorable & cozy cottage sits on the pondside corner of our 25 acre property. Deck is great for BBQ and stargazing at night. Enjoy fire pit on the beach for s’mores. Pool not heated but hot tub can be heated. Sauna in gazebo. Enjoy the canoe and fish in our private pond (carp & bass) Lots of hiking trails nearby and great restaurants. 20 mins. from Harlem-Valley Wingdale train station. Car is highly recommended as taxi service is limited.

4.89 out of 5 average rating, 110 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

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.

4.98 out of 5 average rating, 45 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