Vacation rentals with a pool in Westchester County

Riverfront Cottage Retreat & Pool 35 mins from NYC

Experience the charm of Actress Misty Rowe's former home (Hee Haw, Brady Bunch, Love Boat)! This historic cottage boasts rustic elegance on its river-facing deck, perfect for entertaining. Cozy living room with stone fireplace, modern kitchen amenities, and in the midst of nature. Unwind by the pool or gazebo, enjoy stunning river views and wildlife spotting. A tranquil retreat with all the amenities for unforgettable memories, just 5 minutes from downtown and 35 minutes from NYC. Exquisite!

The Perch, a luxe cottage with pool 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. The newly renovated cottage is thoughtfully designed to provide a cozy and inviting atmosphere.

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. 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 pool now opened!

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

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 Mountain Lakes Park. Horse shows at Old Salem Farm, apple picking, farmers markets, great restaurants and NYC bound train nearby. 3 bedrooms + finished basement sleeps 7 and has all the comforts of home, including a kitchen stocked with culinary tools and staple ingredients. Great wifi and 2 desks makes it easy to work remotely!

Harborview/pool/freeparking/downtown

Cozy 1 bed harbor view apt At harbor point Stamford. Centrally located, 5 min walking distance from train station, close to uconn shopping mall and restaurants…. In unit washer/dryer. tv in bedroom and TV in living room. Queen size bed, sofa bed also twin size air mattress and baby pack and play available. Family friendly, Please feel free to contact me if need any accommodations I will do my best to accommodate my guests :) No parties or large group of people allow in the unit.

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.

City Escape | Heated Pool | Hot Tub| Fire Pit

Welcome to our charming house located in the picturesque town of Mahopac, NY. This stunning property is perfect for families or small groups of friends looking for a peaceful and relaxing getaway. Our house boasts three spacious bedrooms with comfortable beds, three modern bathrooms, and gorgeous vaulted ceilings throughout. You'll love the bright and airy feel of the house as well as the tasteful decor and comfortable furnishings.

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!