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

Barn in Roxbury

5 out of 5 average rating, 35 reviews

Classic Red Barn with game room

Enjoy a fun and romantic stay in this renovated classic red barn on a private country property. The barn is only available when the main house is unoccupied, so you will have the whole barn, with game and fitness rooms, and the full run of the beautiful private country exterior property. If you're lucky, you'll get a visit from the horses at the neighboring horse farm! The barn's game room has a couch, ping pong and pool tables, basketball hoop outside, and a separate exercise and boxing space.

Guest favorite

Rental unit 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.

Superhost

Home in Litchfield

4.91 out of 5 average rating, 47 reviews

Woodland Country Retreat: 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 by the firepit w/loved ones! 11/9/24: Accepting inquiries on block dates. Pool deck area in rear of house is closed under maintenance work.

Guest favorite

Rental unit in Kent

4.92 out of 5 average rating, 144 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

Home in Bethlehem

5 out of 5 average rating, 34 reviews

Lakeview Expanse

This is a renovated house situated on 14 acres in Litchfield County, CT. This is a 5 bedroom estate - 1 king size bed, 3 queen beds, 1 bedroom is a dedicated office with a queen size air mattress. 8 guests maximum. Heated saltwater pool (closed until May 2025), 5 seater/1 lounger hot tub, 2 outdoor dining area (one on deck, other on pool patio), 8 seater dining table, 4 seater breakfast table in kitchen, extra large jacuzzi in primary bathroom, wood burning fireplace. Completely private

Guest favorite

Home in Goshen

5 out of 5 average rating, 53 reviews

Superb Lakefront Getaway Perfect for the Holidays

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

Guest favorite

Home in Roxbury

5 out of 5 average rating, 13 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.

Superhost

Home in Morris

4.9 out of 5 average rating, 91 reviews

Luxury Compound, Pool, Gym, Tree House, Game Barn

Serene, elegantly appointed 19th century farmhouse compound that has been fully modernized and set on the edge of a 50 acre land preserve and state park that borders boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this l expansive home has every amenity: gas fireplace, pool, hot tub, heated gym, dry sauna, two chef’s kitchens, a primary suite with wb fireplace and soaking tub, a pool house guest suite, and secluded 3-story treehouse w/ slides and swing set.

Superhost

Home in Sherman

5 out of 5 average rating, 4 reviews

Designer's Historical 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.

Guest favorite

Guesthouse in New Milford

5 out of 5 average rating, 22 reviews

Cozy House in the Trees w/ Fireplace

This cozy, private guest house, situated on 20 wooded acres was once part of the artist, F. Luis Mora's estate. A peaceful and relaxing place to be with family and friends. The house is located less than 2 hours from NYC and only 15 mins from both New Milford and Kent. The house is set in an excellent location to explore the Litchfield Hills, the Housatonic Valley and see some of the best Fall foliage in New England. A prime location for some of the most scenic hikes in the area.

Guest favorite

Home in Litchfield

4.99 out of 5 average rating, 79 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.

Guest favorite

Cottage in Kent

4.89 out of 5 average rating, 79 reviews

1 bed pond cottage

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 & hot tub closed for the season. Sauna is open all year round. Enjoy the canoe and fish in our private pond (carp & bass) Lots of hiking trails nearby. 20 mins. from Harlem-Valley Wingdale train station. @geermountainfarm @cloverandivyevents