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Holiday 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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Bungalow in Morris

4.94 out of 5 average rating, 63 reviews

Cozy Pool House with Treehouse, Grill, & Game Barn

Magical bungalow retreat with pool, cedar sauna, steam shower, game barn, gym and three story treehouse in bucolic country setting. Surrounded by protected lands great for hiking and tons of summer and winter activities including Bantam Lake, Mt. Tom skiing and snowboarding, and endless White Memorial Foundation trails. This is a private pool house located on a small compound. Absolute privacy with your own parking, entrance, heating system, and very secluded setting at the back of the property.

21–28 Aug

$1,034 SGD per night

Guest favourite

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.

6–13 May

$400 SGD per night

Guest favourite

Flat 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.*

21–28 Oct

$209 SGD per night

Guest favourite

Home in Bethlehem

5.0 out of 5 average rating, 18 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 for the winter), 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.

2–9 Oct

$1,495 SGD per night

Guest favourite

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

27 Mar – 3 Apr

$809 SGD per night

Guest favourite

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.

30 Sep – 7 Oct

$748 SGD per night

Guest favourite

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.

22–29 Dec

$563 SGD per night

Guest favourite

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.

22–29 Sep

$1,402 SGD per night

Guest favourite

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.

3–10 Nov

$471 SGD per night

Guest favourite

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!

16–23 Feb

$858 SGD per night

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!

16–23 Aug

$318 SGD per night

Guest favourite

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.

8–15 Nov

$1,030 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Litchfield County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Warren

5.0 out of 5 average rating, 27 reviews

Moody Pond House: Brand New Weekend Country Escape

12–19 Jun

$1,279 SGD per night

Guest favourite

Home in Kent

4.91 out of 5 average rating, 11 reviews

Perfection in Litchfield County, 5 BR with Pool

18–25 Jun

$833 SGD per night

Guest favourite

Home in New Milford

5.0 out of 5 average rating, 8 reviews

1780’s farm house full of charm and modern comfort

25 Mar – 1 Apr

$1,099 SGD per night

Guest favourite

Home in Warren

5.0 out of 5 average rating, 19 reviews

"Melius" PoshPadsCT Pool Tennis Ski Trampoline 5*

18–25 May

$1,254 SGD per night

Guest favourite

Home in Wolcott

4.95 out of 5 average rating, 19 reviews

Amazing GParadise w/King Bed, Private Pool and BBQ

20–27 Apr

$909 SGD per night

Guest favourite

Home in New Milford

5.0 out of 5 average rating, 9 reviews

Spacious and relaxing New Milford 5br home w pool!

11–18 Oct

$999 SGD per night

Home in Litchfield

4.7 out of 5 average rating, 100 reviews

Prana Residence Spa Indoor Pool

29 Jan – 5 Feb

$1,202 SGD per night

Home in Bethlehem

4.86 out of 5 average rating, 28 reviews

Long Meadow Manor- Heated Pool, near U-pick farms

26 Jun – 3 Jul

$937 SGD per night

Destinations to explore