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.

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Guest favorite

Home in Yonkers

5 out of 5 average rating, 7 reviews

Classic Luxury Home in Prime Location!

Relax with the whole family at this beautiful, peaceful place to stay. Come and enjoy our recently renovated property, fully equipped for your stay in New York. Tranquil backyard features a swim spa/hot tub and lots of outdoor space to relax. Large second floor balcony also allows for outdoor relaxation. Minutes from major roads - I87, Saw Mill Parkway, Cross County Parkway, all within a 5 minute drive. Just blocks from public transport links - bus which takes you directly to MTA NYC Subway.

Guest favorite

Guest suite in Croton-on-Hudson

4.98 out of 5 average rating, 125 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.

Guest favorite

Home in Stamford

4.95 out of 5 average rating, 240 reviews

Midcentury Modern ZenHouse Sculptor Studio

ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen. Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations!

Guest favorite

Cottage in Putnam Valley

4.93 out of 5 average rating, 69 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.

Guest favorite

Home in Greenwich

4.97 out of 5 average rating, 36 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Experience the charm of Actress Misty Rowe's former home (Hee Haw, Brady Bunch, Love Boat)! This historic cottage boasts rustic elegance on its river-facing deck, perfect for entertaining. Cozy living room with stone fireplace, modern kitchen amenities, and in the midst of nature. Unwind by the pool or gazebo, enjoy stunning river views and wildlife spotting. A tranquil retreat with all the amenities for unforgettable memories, just 5 minutes from downtown and 35 minutes from NYC. Exquisite!

Guest favorite

Home in Yorktown Heights

4.9 out of 5 average rating, 135 reviews

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. 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.

Guest favorite

Home in Bedford

5 out of 5 average rating, 25 reviews

The Waterside Home - Pool, Tennis, Sauna & Golf

Relax or work in this wonderfully spacious and well-equipped home! Play tennis or pickleball on the private court? Swim in the amazing pool? Enjoy outdoor sauna? Walk the 9-acre gardens? Play golf at great courses nearby? Whether for a romantic treat or simply a relaxing time with the family, this home is waiting for you. Magnificently situated in a woodland overlooking the Cross River reservoir. Close to all amenities, airports and routes. 6 minutes by taxi from the Katonah train station.

Guest favorite

Barn in Katonah

4.97 out of 5 average rating, 117 reviews

The Magic Red Barn

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

Guest favorite

Rental unit in Stamford

5 out of 5 average rating, 33 reviews

Stamford Grand Apartment + Cozy Den

Welcome to your luxurious One-Bedroom + Den home at The Asher in downtown Stamford. Enjoy the vibrant city life with cafes, brunch spots, bars, and fine dining just steps away on Bedford Street. Highlights: - Request to be on the 4th floor or higher - Deep-clean prior to every guest - Coffee, fresh linens, & bathroom essentials provided - Co-working Lounge & Conference Rooms - 24/7 fitness centre & yoga room - Rooftop Pool and Lounge - Outdoor Grill Stations - LED recessed lighting

Guest favorite

Guesthouse in Bedford Hills

5 out of 5 average rating, 26 reviews

The Perch, a luxe cottage in the woods 1h from NYC

"The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa The Perch, our luxe cottage nestled in the woods in Bedford, NY is the perfect country getaway. Surrounded by nature, this charming retreat offers a perfect getaway for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC. The newly renovated cottage is thoughtfully designed to provide a cozy and inviting atmosphere.

Guest favorite

Home in Englewood

4.93 out of 5 average rating, 144 reviews

Englewood NJ Country Carriage House (15 min NYC)

Spacious eclectic luxurious renovated carriage house on 1 acre with a pool & hot tub, & a separate private 6 seat 60 jet hot tub, sauna, steam room, gas & wood burning fire pits, pool/ping pong table, trampoline & basketball court in a gorgeous quiet suburb of NYC. In 20 minutes you can be enjoying all that NYC has to offer & then come back for a sauna & steam. Great small reunion/intimate party space!

Guest favorite

Home in Pound Ridge

5 out of 5 average rating, 148 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.