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!

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.

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.

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.

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.

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!