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

A spacious guest room features a large bed with light pink bedding, complemented by artwork on the wall. Natural light fills the room through multiple windows, highlighting a seating area with a curved couch and a glass coffee table on a patterned rug. A small desk and mirror are also present.

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

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.96 out of 5 average rating, 245 reviews

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! 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

Guest favorite

An inviting outdoor pool is surrounded by lush greenery, creating a serene atmosphere. Decorative planters enhance the space, while a stone patio provides a functional area around the pool. Sunlight filters through the trees, casting gentle shadows on the water's surface.

Home in Yorktown Heights

4.9 out of 5 average rating, 144 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

A clear blue pool is centered within a lush green landscape, surrounded by neatly trimmed hedges and tall trees. Comfortable lounge chairs are positioned around the pool area, offering a serene spot for relaxation. The scene is bright and inviting under clear blue skies.

Home in Bedford

5 out of 5 average rating, 26 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

A heated saltwater pool is surrounded by a spacious, fenced lawn. The pool area features wooden decking and chairs for relaxation. Towering green trees provide a natural backdrop, emphasizing the tranquil outdoor setting near the private barn.

Barn in Katonah

4.97 out of 5 average rating, 119 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

A serene backyard scene is presented, featuring a sparkling pool surrounded by gray lounge chairs. Lush green trees create a privacy barrier in the background, while a garden area and fencing add to the charm of the outdoor space.

Home in North Salem

4.93 out of 5 average rating, 30 reviews

North Salem Home with Pool & Great Yard

Relax by pool, curl up by the fireplace or bbq on the covered patio at our pet friendly home in bucolic North Salem. Hike the nature preserve on the street or Mountain Lakes Park. Horse shows at Old Salem Farm, apple picking, farmers markets, great restaurants and NYC bound train nearby. 3 bedrooms + finished basement sleeps 7 and has all the comforts of home, including a kitchen stocked with culinary tools and staple ingredients. Great wifi and 2 desks makes it easy to work remotely!

Guest favorite

Home in Port Chester

5 out of 5 average rating, 31 reviews

The All Seasons Oasis!

Welcome to paradise! Unwind by the pool, soak in the hot tub, relax w/ family & friends in our private outdoor patio & serene entertaining spaces inside. Open floor concept house w/ welcoming living room, large dining room, chef's kitchen, billiards/game room w/ TV, reading room, & more. 4 bedrooms, 5 beds, 2.5br, 2 couches - including Primary w/ King+Ensuite br. Close to Rye/Greenwich/White Plains/Rye Beach/Playland/Capitol Theatre/Parks/Shops/Restaurants/Easy highway access.

Guest favorite

A serene saltwater pool is surrounded by well-maintained grass and lush greenery. Natural stone pavers outline the pool area, providing a harmonious blend with the surrounding landscape. Several lounge chairs are positioned nearby for relaxation, enhancing the outdoor atmosphere.

Guesthouse in Bedford Hills

5 out of 5 average rating, 33 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 is the perfect getaway in any season 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.

Superhost

The exterior showcases a large, charming home with a mix of brick and wooden accents. Spacious parking is available on the driveway. Windows reflect warm lighting from inside, surrounded by leafy trees creating a serene atmosphere.

Villa in Ossining

4.8 out of 5 average rating, 111 reviews

Castle - Winter Wonderland - Cross Country Skiing

Fall - Autumn Paradise at Westchester Castle: Your Sunny Group Getaway! 7 Bedrooms, 4 Bathrooms: Sleeps 13 with varied bed types for comfort. Entertainment Galore: Smart TV, pool table, board games. Gourmet Kitchen: Fully equipped for all culinary needs. Relaxation: In-ground pool and indoor tub. Convenience: Free 100 Mbps WiFi, self-check-in/check-out, washer & dryer. Nearby Attractions: Close to parks, family spots, dining, and more!

Guest favorite

A rustic exterior of the retreat is surrounded by lush greenery, showcasing a mix of wood and stone finishes. Outdoor seating is provided around a fire pit, nestled amidst landscaped areas. Large windows reflect the natural surroundings, allowing for integration with the serene environment.

Barn in Mount Kisco

5 out of 5 average rating, 7 reviews

Chic Barn Retreat w/ Fireplace, Hike, firepit

Welcome to The Barn Retreat! This unique getaway blends rustic charm with modern comfort—half vintage barn, half stylishly renovated living space. Nestled on 5 private wooded acres, enjoy nature with a grill, fire pit, and seasonal pool. Perfectly located near shops, hiking trails, and serene lakes, it’s an ideal escape for families, friends, and furry companions. Unwind, explore, and make lasting memories in this pet-friendly haven!

Guest favorite

A charming carriage house features large windows and a high peaked roof, set amidst lush greenery. A well-maintained pool with a gentle fountain is situated in front, surrounded by landscaped gardens and inviting white lounge chairs.

Home in Englewood

4.93 out of 5 average rating, 149 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

A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

5 out of 5 average rating, 153 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.