Holiday rentals with a pool in Westchester County

Gameroom, backyard + pool! 7m 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/ 55" 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 toGrand Central)

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

Stamford Grand Apartment + Cozy Den

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

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.

Billy Joel/JP Morgan Hudson Valley Home 1h to NYC

Come stay in J.P. Morgan's summer home with breathtaking views of the Hudson River! Private saltwater pool & sauna. Billy Joel famously also lived here in the 1970s when he wrote "New York State of Mind" and "Summer, Highland Falls" in the primary bedroom. This is J.P. Morgan's original "Cragston" mansion (he used to take his Yacht up here from Wall Street!). Under 5 minutes to West Point & Bear Mountain 1 hour to NYC Cold Springs & Peekskill are under 20 minutes away

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.

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 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. **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.