Vacation rentals with a pool in Rockland County

Pool + Perfect NYC Getaway 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!

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.

Cozy Family Chateau Close to NYC avail Longterm

Impeccably Clean & Private, 35 min drive into NYC, Unique living space on 4 levels. Private entrance to office, surround sound, 2 Fireplaces, 3 bedroom, 3 bathroom. Beautiful kitchen to cook and socialize around. The sunroom is furnished for reading a book under the sun and among the greenery. Main dining table seats 8. Heated pool with sun deck and hot tub. Outdoor barbecue & new patio. Additional patio off bedroom. Great hiking and trails nearby. This property is the perfect family getaway.

Group Spring Retreat | Fun Games & Gourmet Kitchen

Enjoy warm weather at this peaceful mountain retreat just an hour from NYC. Lounge on the patio with a BBQ, fire pit, or spacious backyard with stunning views, or cool off in the pool and jacuzzi. 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. This home is a serene escape for the whole group!

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.

A house where the whole family fits perfectly.

Welcome to your perfect home away from home! This beautifully designed space offers comfort, style, and everything you need for a relaxing stay. you will enjoy a cozy atmosphere paired with modern amenities. Located in a safe, beautiful, convenient, and vibrant neighborhood, you will be at just 40 minutes away from major attractions (New York city Times Square, American Mall, the Meadowlands complex sport, Yankee Stadium, Bear Mountain, Woodbury Commons, and more).

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.

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!

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 14, 2024, before it reopens in May 2025. This smart 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!

'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.

Private Suite in the Heart of the Hudson Valley

Private suite in Croton-on-Hudson with its own entrance, full bath, and a striking 6-ft circular window overlooking the trees. Enjoy access to an outdoor fire pit, on-site parking, and easy transit via nearby Metro-North stations. Pet friendly and close to the Hudson River, great restaurants, hiking trails, and scenic overlooks—an ideal base to explore the beauty of the Hudson Valley by day and return to a cozy retreat at night.

Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Colonial Retreat w/ Pool, Hot Tub & Game Room! This stunning home in Stony Point sits on 1.16 acres and sleeps 28 guests across 9 bedrooms and 3.5 baths. Enjoy an open floor plan, high ceilings, a cozy fireplace, and a fully equipped kitchen. The game room is on the first floor near the dining room. Relax on the deck, soak in the private hot tub, or enjoy the seasonal pool. Close to hiking, dining, and shopping!