Holiday rentals with a pool in Westchester County

Designer 1BR | Luxe Amenities, Gym, Parking

Welcome to your luxury White Plains escape, a modern one-bedroom retreat with all the comforts of home and the amenities of a five-star resort. • Deep-cleaned before every stay • Rooftop green, coworking lounge and private pods • Game room with virtual golf, pinball and shuffleboard • Resort-style seasonal pool (Open May-Sept.) with deck, grills and fireside lounge • State-of-the-art fitness center with on-demand classes • Steps from restaurants & shops; easy walk to Metro-North to NYC (45min)

Westchester Winter - Fireplace Pet Friendly Events

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 Arcade Games, Smart TVs, and fast WiFi. Fully equipped kitchen and pet-friendly. Nearby winter highlights include Sleepy Hollow, Rockefeller State Park Preserve snowy trails, Croton Gorge Park frozen waterfalls, Hudson RiverWalk views, and Bear Mountain Snowy Trails. Perfect for family or group stays. Events are welcome, contact us in Airbnb for more details!

Arkadia House Mid-century retreat with pool & view

Located only 75 minutes from NYC, this architectural mid-century retreat is immersed in the scenic beauty of the Hudson Valley. The towns of Cold Spring & Beacon are just a few minutes drive away. As are numerous hikes, such as Breakneck Ridge & Bear Mountain State Park. The area is full of activities from farmers markets, golf, kayaking and galleries (Dia: Beacon, Magizzino). The sparkling pool and garden is perched above the Hudson River with sweeping views. (Pool closed Nov-end of April)

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

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.

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 many others in town. Horse shows at nearby Old Salem Farm, apple picking, farmers markets, great restaurants and close NYC bound train. 3 bedrooms sleeps 6 and has all the comforts of home like a kitchen stocked with culinary tools and staple ingredients. Central A/C, great wifi and 2 desks makes it easy to work remotely!

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.

Luxury 2 BR Apt with Gym and Pool

This modern high-rise offers luxury one & two bedroom residences with floor-to-ceiling windows showcasing Long Island Sound and Manhattan views. Enjoy gourmet kitchens, sleek bathrooms, and in-unit washers and dryers. Amenities include a rooftop pool, fitness center, sauna, outdoor terrace with a pizza oven, multi-sport simulator, and more. Located minutes from downtown and the Metro-North, 3Thirty3 combines luxury, comfort, and easy access to dining, shopping, and NYC.

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.