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

5.0 out of 5 average rating, 15 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.

May 3 – 10

G$60,072 GYD per night

Guest favorite

Apartment in Kent

4.93 out of 5 average rating, 127 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.*

Oct 29 – Nov 5

G$32,313 GYD per night

Guest favorite

Home in Morris

4.91 out of 5 average rating, 64 reviews

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

Serene, elegantly appointed historic 19th century farmhouse and compound that has been fully modernized and set on the edge of a 50 acre protected forest that borders spring fed Bantam Lake. Located in the rolling hills of Litchfield County this surprisingly expansive home has been updated with every amenity: pool, hot tub, gym, chef’s kitchen, primary suite with fireplace and soaking tub, pool house guest apartment, gas fireplace in living room, and a magical treehouse in the 3 acre yard

May 7 – 14

G$93,982 GYD per night

Guest favorite

Home in Goshen

5.0 out of 5 average rating, 46 reviews

Superb Lakefront Getaway with Family and Friends

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

Oct 1 – 8

G$186,074 GYD per night

Guest favorite

Guest suite in Cornwall

4.92 out of 5 average rating, 73 reviews

A little slice of paradise in Northwest CT!

A beautiful, spacious, very private apartment just for you. Just steps from Kent Falls State Park, the beautiful Housatonic River, apple picking - it’s all here! Plenty of parking, quiet living. You’ll have all the amenities for a weekend or for a much needed longer stay in the country. Litchfield County is the perfect destination in all four seasons! Your hosts will help to make you comfortable whether you have come for an event, to eat and shop, to explore, or just for peace and quiet.

Dec 10 – 17

G$37,790 GYD per night

Guest favorite

Home in Litchfield

4.94 out of 5 average rating, 33 reviews

Woodland Country Retreat w/ Pool Near Wineries

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 the 4-bedrm, 2-bathrm vacation rental. 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 for poolside bbq w/loved ones! July & August: monthly rental only. Early bird special avlbl.

Sep 29 – Oct 6

G$112,159 GYD per night

Guest favorite

Cottage in Litchfield

4.98 out of 5 average rating, 65 reviews

Cottage on Litchfield Farm

This is a newly constructed first floor cottage apartment, designed in an urban industrial farmhouse style, situated on a 28 acre farm in the historic town of Litchfield, CT. This restored farm includes an owner occupied main house, heated saltwater pool with a pool house, a barn with 3 goats, 2 miniature donkeys, 2 bunnies, a vegetable garden, beautiful estate flower gardens, and an apple orchard. Beginning October 2020, newly renovated office/classroom space included in rental.

Dec 20 – 27

G$84,443 GYD per night

Guest favorite

Home in Morris

5.0 out of 5 average rating, 18 reviews

Historical Luxury Farm House w/ Guest House

4BR/3BA Litchfield Estate Home on 2 acres and connected to the 600 acre Camp Columbia State Park. Kick back and relax in this calm, stylish space with multiple outdoor sitting areas. This 1750's Morris Founder's home is filled with modern amenities, a guest house, pool, and barn. Located 5 miles south of the town of Litchfield and a quick drive to Washington. Minutes away from amazing restaurants, Bantam Lake, skiing, hiking, mountain biking, and so much more.

Oct 20 – 27

G$172,876 GYD per night

Guest favorite

Home in Warren

5.0 out of 5 average rating, 16 reviews

Farm Valley Cottage + 60 ft Pool

Country getaway, light filled 3-bedroom cottage, private 60' pool with sweeping farm valley views, plus guest studio. Nestled on 7 acres of nature, where a flock of chickens and one very friendly free ranging turkey 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.

Nov 3 – 10

G$70,634 GYD per night

Guest favorite

Home in New Hartford

4.91 out of 5 average rating, 11 reviews

Mountain Serenity Lake View Pool & Hot Tub

Unwind above tranquil waters, marinate in the heated pool, bundle beneath the blanket as the crackling fire radiates warmth, savor freshly roasted coffee perched on the mountain, unify with nature or imbibe libations with friends, this property affords serenity for all. Steps from skiing, fishing, hiking, golfing, tubing or boating, you will depart rested, restored and renewed. Hot tub overlooking lake for the winter season!

Apr 9 – 16

G$128,719 GYD per night

Superhost

Guest suite in Watertown

5.0 out of 5 average rating, 4 reviews

Hidden Serenity at TuKasa - Pool & Billiards

Discover serenity in our private Airbnb nestled in the heart of Litchfield County. Embrace tranquility surrounded by nature, with a dedicated workspace for productivity. Dive into relaxation with a billiards/bar room with games, a refreshing pool (during summer months), outdoor table, and firepit at your fingertips. Your perfect retreat awaits!

Oct 7 – 14

G$34,929 GYD per night

Guest favorite

Home in Morris

4.97 out of 5 average rating, 31 reviews

Chic restored barn on 6 acr with saltwater pool

A sublime and oh-so-comfy retreat from the vicissitudes of life (and the pandemic), Barn farm --conceived and designed by the former Artistic Director of Ralph Lauren -- is a mix of small touches, thoughtfulness, and simple country beauty. A restored 1860 barn and milking parlor, we are less than 2 hours from NYC. 3 hrs from Boston.

Apr 14 – 21

G$154,440 GYD per night