Holiday 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

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.

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.

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!

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.

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.

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!

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.