Holiday rentals with a pool in Westchester County

Perfect NYC Getaway with Pool in the Hudson Valley

Just 3 minutes from the Cortlandt station and 7 minutes from the Croton-Harmon train station, this private house is only a 48 minute ride on the Metro-North train from Grand Central Station in NYC, yet it is the ultimate escape from the city. Nestled in the woods, the house is exceptionally charming and peaceful. Croton has long been beloved by naturalists, and the area has incredible hiking trails, quaint coffee shops, restaurants, and more. Don’t forget to visit the stunning Croton Dam nearby!

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

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

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers blooming in June, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool and cedar soaking tub. Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Hudson Valley Pool Retreat · 50min to NYC · 3 Acre

Willoway is your private 3+ acre Hudson Valley retreat — a heated 36,000-gallon saltwater pool, distant Hudson River sunset views, and woodland quiet, all 50 minutes from Grand Central by train. Wake to birdsong on the deck, swim until the sky turns orange, dine al fresco for six on the stone patio, and fall asleep by the stone fireplace. Three bedrooms sleep six. Single-level home, gated drive, self check-in, dogs welcome. In my family for 60+ years and still cherished — now yours to enjoy.

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

Stamford Grand Apartment + Cozy Den

Welcome to your luxurious One-Bedroom + Den home at 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

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

Peaceful Light-Filled Guesthouse salt pool/sauna

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, or unwind in the pool side sauna.. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

House on the hudson is a 3bed 2bath private kit/LR

Happy Fall our home is very near Apple picking farms and the pool is still open. A minutes drive to Historic and legendary HV activities. Minutes from Sleepy Hollow. Tons of farms wineries distilleries and breweries too. Summer fun kayak rentals near by. We have tons of hiking or biking trails minutes from our front door. Our deck overlooking the Hudson River and hook mountain even spark a camp fire or roast some s’mores