Vacation rentals with a pool in Westchester County

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

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!

Stamford Grand Apartment

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 before 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

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.

A Lovely Cottage in the Woods with Private Pool

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.

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.

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!

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.

Wonderful home w/ outdoor space + Pool/Hot tub

Let all your day-to-day worries fade away in this beautifully home! Private sanctuary which includes a dedicated office space, fireplace, swimming pool, hot tub(soon) deck & much more. This is your little piece of heaven. A private oasis 20 minutes from NYC. Lots of room to hang, play games, watch movies and more. Plenty of free street parking available! Enjoy!!