Vacation rentals with a pool in Westchester County

Perfect NYC Getaway in the Hudson Valley

Just 3 minutes from the Cortlandt station and 7 minutes from the Croton-Harmon train station, this private house is only a 48 minute ride on the Metro-North train from Grand Central Station in NYC, yet it is the ultimate escape from the city. Nestled in the woods, the house is exceptionally charming and peaceful. Croton has long been beloved by naturalists, and the area has incredible hiking trails, quaint coffee shops, restaurants, and more. Don’t forget to visit the stunning Croton Dam nearby!

Westchester Winter - Fireplace Events Pet Friendly

Winter retreat at The Westchester Manor, cozy 5BR, 4BA villa for 13 guests in Ossining. Unwind by the in-house bar, pool table, relax with Smart TVs and fast WiFi. Fully equipped kitchen and pet-friendly. Nearby winter highlights include Sleeply Hollow, Rockefeller State Park Preserve snowy trails, Croton Gorge Park frozen waterfalls, Hudson RiverWalk views, Tarrytown holiday lights and Bear Mountain WinterFest. Perfect for family or group stays. Events welcome, contact us in Airbnb for details!

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

The All Seasons Oasis! Hot tub +Games +Near Train

Welcome to paradise! Unwind by the pool (open May-Sept), 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.

Gameroom, backyard + pool! 5m 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/ 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)

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage combines rustic elegance with modern comfort. Relax by the stone fireplace, cook in the full kitchen, or step onto the river-facing deck to enjoy peaceful views. Outside, unwind in the heated pool or year-round hot tub, gather by the gazebo, or spot wildlife along the river. Utilize the fire pits and more. A tranquil retreat just 5 minutes from downtown Greenwich and 35 minutes from NYC.

Cozy 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, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. 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.

The Magic Red Barn with Heated Salt Pool

Experience countryside magic just one hour from NYC! Enjoy nature’s wonderland, nearby farmers’ markets, and scenic trails. Indulge in our heated saltwater pool for a perfect retreat. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn featuring: 1 king, 2 queen, 1 toddler bed, full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests seeking escape. Enjoy complete privacy—no other guests. Fiber optic Wi-Fi.

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

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 with a heated saltwater pool in Bedford, NY is the perfect country getaway. Surrounded by nature, this charming retreat is the perfect escape in any season for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC. **Pool closed for the season, will re-open late May 2026**

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Private Suite in the Heart of the Hudson Valley

Private suite in Croton-on-Hudson with its own entrance, full bath, and a striking 6-ft circular window overlooking the trees. Enjoy access to an outdoor fire pit, on-site parking, and easy transit via nearby Metro-North stations. Pet friendly and close to the Hudson River, great restaurants, hiking trails, and scenic overlooks—an ideal base to explore the beauty of the Hudson Valley by day and return to a cozy retreat at night.