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)

Luxury Private Apt with Gym

Enjoy a fireside lobby, a game gallery with vintage pinball and skee-ball, a virtual golf simulator, and an indoor putting green. Stay active in the state-of-the-art fitness center or unwind in the poolside clubroom with a demonstration kitchen. Work comfortably in the coworking space with quiet pods and communal seating. Outdoor amenities include a pool deck with cabanas, a rooftop lounge with billiards and chess, and dining areas with grills. Pet-friendly perks like a dog spa and a bike room c

Westchester Summer: Pool Pet Friendly Events Games

Spring and summer escape at The Westchester Manor, a spacious 5BR, 4BA Tudor for up to 13 guests, pet-friendly. Enjoy sunny days by the pool, unwind at the custom in-house bar, and relax with arcade games, pool table, Smart TVs, and fast Wi-Fi. Fully equipped kitchen and in-unit laundry included. Located under 1 hour from MetLife Stadium, East Rutherford, host of the FIFA World Cup 2026. Near Sleepy Hollow, Croton Gorge Waterfalls, and Bear Mountain. Events are welcome, message 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

Enjoy Summer Living "Stone Haven" Hudson Valley

Luxurious, spacious two story private living quarter located in the Hudson Valley. We offer modern lodging with a brand new small kitchen and bath outfitted with marble including complementary coffee & tea bar. A large living room is a great spot to watch a movie , shoot some pool or lounge around after a day of work or leisure. Enjoy amenities, salt water pool, luxurious bedding, quiet work space with High Speed WiFi. Minutes from hiking & bike path, restaurants, train station to NYC.

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.

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.

The Perch: Saltwater Pool Woodland Cottage Retreat

The Perch, a design-forward woodland cottage surrounded by nature just one hour from NYC perfect for couples escaping the city for a quiet Hudson Valley weekend. Spend slow mornings overlooking the woods, afternoons by the saltwater pool, and evenings exploring Bedford’s historic village restaurants and trails. "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa *Pool re-opens late May through mid-Sept* inquire for details