Vacation rentals with a pool in Westchester County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Westchester County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 94 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Set in historic 1750's farmhouse, located in the center of Teatown Lake Reservation with over 1,000 acres of trails in our backyard, this elegant getaway has all the luxuries of a resort (pool, cedar barrel sauna, spa tub, rain shower) while maintaining the rustic charm of a working farm. Easily accessible to NYC, yet worlds away-- a chic private refuge where you can unwind and restore to the gentle sounds of nature (& the occasional rooster.) Friendly dogs and artists:) Sorry, no kids or pets.

Feb 12 – 19

G$47,700 GYD per night

Guest favorite

Home in Stamford

5.0 out of 5 average rating, 36 reviews

Gameroom, backyard + pool! 7m to train + downtown

Welcome to our family-friendly 2-story Cape Cod! Enjoy a private fenced-in pool, game room and: - Expansive fenced backyard w/ grill + pool - Game room: foosball table w/ 55" Roku TV - 4 bedrms: 2 king, 1 queen, 2 Twin XL, feat beautiful, red hardwood floors - High-Speed 1 Gig Fiber-optic internet & 2 desks - Private parking for 2 cars with additional free street parking - 3 full baths, stocked kitchen, washer/dryer - 8min to Downtown/UConn, 7min to Train Station (50m Express to Grand Central)

Dec 6 – 13

G$78,036 GYD per night

Guest favorite

Home in Greenwich

4.95 out of 5 average rating, 22 reviews

Cottage/Cabin Retreat by River Near Downtown

Perched on the banks of a tranquil river, this charming cottage exudes rustic elegance. A cozy retreat, it boasts a river-facing deck, perfect for morning teas and evening sunsets. Inside, a cozy living room centers around a river stone fireplace, casting a warm, inviting glow. The kitchen features modern amenities, blending seamlessly with the cottage's rustic character. Outside, a well-manicured garden leads to a private deck. The soothing sounds of the river create an enchanting ambiance.

Jun 8 – 15

G$108,054 GYD per night

Guest favorite

Cottage in Putnam Valley

4.98 out of 5 average rating, 46 reviews

Beautiful Cottage in Hudson Valley w/Pool & Views

Welcome to our beautifully renovated and thoughtfully decorated cottage in the charming town of Putnam Valley! Tucked away in a quiet, wooded setting, this cozy retreat is the perfect getaway for couples, families, solo travelers. Enjoy breathtaking sunsets over the Hudson Valley from your private deck, surrounded by lush trees and wildlife. Located just a short drive from the bustling town of Cold Spring, the cottage is perfectly situated for exploring all that the Hudson Valley has to offer.

Sep 2 – 9

G$103,645 GYD per night

Guest favorite

Home in Yonkers

5.0 out of 5 average rating, 11 reviews

Entire home- pool, gym, theater. 10 min from NYC.

Welcome to your home away from home! This is a beautifully maintained 3 BR home, with sleeping space for up to 8 people. BR’s are on the 2nd floor, with the full bathroom. Main floor has living room/dining area and full kitchen as well as a gym (includes treadmill, free weights and bench). Basement has an entertainment room & laundry area. Backyard has island grill & pool w/2 decks. Kitchen stocked w/basics; dishes, cooking supplies, seasonings and grilling utensils. EVERYTHING PRIVATE!

Jun 24 – Jul 1

G$142,086 GYD per night

Guest favorite

Barn in Katonah

4.96 out of 5 average rating, 97 reviews

Magic Red Barn

Winter magic 1 hour from NYC Near Christmas tree farms. 1000 sq ft renovated 2nd floor luxury apartment in a private barn with: -2 queen, 1 king and 1 toddler beds, -a full kitchen (1/2 size fridge and ice tray freezer, microwave and full size oven and range) and bathroom (shower). Magical experience for a family or friends who like a big open space. Fun. NO other guests. Hot tub available. It is a new inflatable Saluspa which heats to 100/104 (weather permitting). Not a hard shell.

Feb 3 – 10

G$92,005 GYD per night

Superhost

Home in Yorktown Heights

4.88 out of 5 average rating, 119 reviews

Cozy winter getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, a huge DECK, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & crib. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Sep 23 – 30

G$70,861 GYD per night

Guest favorite

Home in Stamford

4.97 out of 5 average rating, 220 reviews

Midcentury Modern ZenHouse Sculptor Studio

Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio

Sep 20 – 27

G$107,109 GYD per night

Superhost

Apartment in Stamford

4.93 out of 5 average rating, 14 reviews

Luxe stay in Downtown Stamford w ocean views

Enjoy a clean, stylish experience at this centrally-located apartment in downtown Stamford. Brand new furniture and appliances. Floor to ceiling windows with ocean views. - 5 min walk from Stamford train station with access to Amtrak and MetroNorth. - 5 min walk from downtown restaurants and boutiques. - 10 min walk from of University of Connecticut. Access to gym and indoor pool. For parking, there is paid street parking or a garage a couple of streets away.

Dec 24 – 31

G$40,653 GYD per night

Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 126 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Enter a freshly updated and thoughtfully furnished peaceful home surrounded by 14 acres of ancient trees, stone walls, and open meadows, in the town of Pound Ridge, NY. This natural light-filled guesthouse features all the elements needed to relax and unwind. In the summer months, guests have access to a heated saltwater pool, bask in the sun under a majestic maple tree, and enjoy the outdoor fire pit while stargazing at night.

Sep 23 – 30

G$144,617 GYD per night

Guest favorite

Home in Katonah

5.0 out of 5 average rating, 24 reviews

Contemporary Retreat w/ GameRoom Pool HBO

Just an hour from Manhattan by train or car, come retreat to your own 4 bedroom, 2.5 bath home with private pool. With its gorgeous sunlight and spacious layout, relaxation and comfort will be at the forefront of your stay. Only a 6 minute drive from the heart of downtown and the Katonah Train Station, enjoy the local restaurants, coffee shops and boutique stores knowing that comfort awaits you at the end of the day.

Aug 25 – Sep 1

G$116,380 GYD per night

Guest favorite

Home in Mahopac

5.0 out of 5 average rating, 14 reviews

Farmhouse with Pool Hudson Valley 1 hr from NYC

Beautifully designed Hudson Valley farmhouse only 1 hour from Manhattan. Close to all the great Hudson Valley towns including Beacon, Cold Spring, Katonah, Bedford Hills, Peekskill, Pleasantville, Croton Falls and North Salem. Fifteen minutes to several lakes, great hiking trails, farm stores, breweries, orchards, and pick-your-own farms. Come get cozy by the fire and enjoy everything the Hudson Valley has to offer!

Aug 18 – 25

G$125,228 GYD per night