Holiday rentals with a pool in Rockland County

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Family · Location · Pets

Beautiful 5-Acre Oasis in the Hudson Valley

Welcome to our guest house! We invite you to enjoy our lush, peaceful, 5-acres of land in beautiful Croton-on-Hudson. Drive up the long, picturesque driveway to reveal our two houses (yours and mine) which are fairly far apart, providing you with plenty of privacy in your standalone house. We love when guests explore our entire property and make themselves at home by using our outdoor hammocks, tree swings, pool, fire pit, many chairs, and even a zip line for kids (all shared only with us).

Value · Family · Cleanliness

Woodland Retreat in KJ, Monroe & Chester!

Discover your perfect vacation, or home from work at this serene home retreat centrally located near KJ/Monroe/Chester, NY! 1 hour drive from NYC, you’ll soak in a woodland atmosphere unlike any other. Our unique space is set in the lower floor of a charming, rustic cabin, surrounded by lush greenery and towering trees. Kindly, read the entire listing description to ensure our home meets your needs and expectations, as this is crucial for a 5-star experience, especially regarding location.

Newly Renovated APT|Close to Hospitals|30 mins NYC

Completely & thoughtfully renovated featuring modern furnishings, king size bedroom, work space & huge walk-in closet. Included in your stay, you'll have full access to brand new fully-equipped kitchen with all major appliances (refrigerator, stove top w/oven) and bathroom, high-speed wifi, complimentary coffee, heating, air conditioning in warmer months, laundry room on site, assigned parking space, linens, towels, & cleaning supplies. Accommodates up to 1 guest or a couple comfortably.

Parking · Comfort · Accuracy

Spacious Home w/Pool/Hot Tub, Mins to Parks/Skiing

This stunning 3-bedroom, 4-bathroom home, tucked away in the woods of Monroe, is just minutes from scenic NY state parks, ski resorts, and wineries. Combining modern amenities with rustic cabin vibes, this spacious retreat offers the perfect blend of comfort and style. Nature enthusiasts can explore the private backyard with a lush garden and heated pool. With elegant living spaces, a game room, and an outdoor wraparound deck, guests will enjoy the ultimate mix of relaxation and luxury.

Value · Location · Cleanliness

Group Retreat | Pool, Hot Tub & Gourmet Kitchen

*POOL IS OPEN* Enjoy warm weather at this peaceful mountain retreat just an hour from NYC. Lounge on the patio with a BBQ, fire pit, hot tub, or spacious backyard with stunning views, or cool off in the pool. Inside, bright living spaces filled with natural light, a full gourmet kitchen, and cozy bedrooms with sparkling clean bathrooms make it perfect for families or groups. Explore nearby trails, relax outdoors, or unwind with games and movies indoors. Great for the whole group!

Family · Location · Check-in

Mediterranean villa •pool•hot tub•fire place

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, outdoor fire pit ,Smart TVs, a private hot tub, spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and Legoland. Unwind, explore, and indulge in upscale relaxation year-round.

Value · Family · Hospitality

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Cozy Fireside Gatherings | Deck w/ Wooded Views | 10 Mi to Legoland | Day Trip to NYC Stay and play in Monroe, known as the Lake Region of New York's Hudson Valley! This charming 2-bedroom, 1-bathroom vacation rental cottage offers a laptop-friendly workspace, a well-equipped kitchen, and quiet outdoor spaces. When you're ready to venture, hike to the picturesque Fitzgerald Falls, step back in time at Museum Village, or visit a local brewery or winery!

Location · Value · Outdoor spaces

'54 Stream

Just 40 minutes north of NYC on the edge of Harriman State Park this unique, fully restored, 1954 Airstream is equipped with all the functionality of the modern world. Perched beside a stream and under a purposely built pavilion the Airstream dream comes alive with its own patio, BBQ, fire pit, and charming barn. From Memorial Day to Labor Day, enjoy shared access to our heated saltwater pool—perfect after a day of hiking. Towels provided.

Family · Location · Quiet

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

Escape to your home away from home retreat featuring a heated pool, hot tub, and sauna. Enjoy the pool until October 29, 2026, before it reopens in May 2027. This Colonial home offers a spacious fenced in yard, deck with large grill, and a cozy fire pit lounge. Just 1 hour from NYC, and close to Woodbury Commons Outlet, Harriman State Park, local breweries, wineries, and restaurants. A perfect spot for everyone to unwind and explore!

Value · Family · Backyard

Mansion in the Hills with Pool

Discover the ideal retreat for your family getaway! Nestled on nearly an acre of idyllic countryside, this charming home boasts cathedral ceilings, generously sized bedrooms, 2 main suites, and a new expansive deck overlooking the inviting pool. Step through the door into a haven of gleaming hardwood floors, bathed in natural light pouring through oversized windows.

Cleanliness · Hospitality · Accuracy

Matt’s Cozy Quarters Near NYC w/Outdoor Living

Peaceful and beautifully renovated 3BR/2BA home in NY with seasonal pool access (May 15–Oct 1), outdoor living space, off-street parking, and quick access to NJ via the Palisades Parkway. Close to shops, dining, and local attractions while offering a quiet, relaxing retreat.

Location · Family · Quiet