Vacation rentals with a pool in Litchfield

Find and book unique homes with a pool on Airbnb

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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Guest favorite

Home in Hamden

4.92 out of 5 average rating, 103 reviews

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

Guest favorite

Guesthouse in Southbury

4.94 out of 5 average rating, 309 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).

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, 145 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 Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

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, 54 reviews

Lakefront Getaway! Location, Views + Style

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

Barn in Bloomfield

4.97 out of 5 average rating, 119 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. Basque 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

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

Barn in Bethel

4.98 out of 5 average rating, 222 reviews

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Guest favorite

Guest suite in Holmes

4.98 out of 5 average rating, 189 reviews

Fall getaway! Huge, Eclectic suite 1.5 hr to NYC!

1.5 hrs from NYC; minutes driving from hiking trails; 20 min from Beacon and Cold Spring! The bottom floor of this 1865 Carriage House has been transformed into an eclectic retreat. The 2500 sq ft private apartment has a room for every mood and super unique decor in every corner! There is also a vintage/antique shop on the property— 20% off for our guests ;)