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.

HtdPool*PvtGym*HotTub*TheaterRm*Swingset*InNature!

NEW LISTING! This 5,100 home is the perfect spot for families looking to enjoy some wholesome fun. Situated on 1.5 acres and nestled between trees and nature, a stay at Suffern Estate is all you need to reset your mind. Rustic charm with a modern feel, this home was built to accomodate generations. Featuring a heated pool, hot tub, movie theater, home gym, swingset, and fully stocked with everything you need to move in for the week. Close to major arteries, yet tucked away for maximum privacy.

Perfect NYC Getaway with Pool 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).

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.

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.

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.

Beaux-arts Summer House

Step back in time in this spacious 1890s Victorian in historic Piermont, NY. Walking distance to Piermont village restaurants and bars, local hiking trails, 35 min to NYC and 40 min to Rutherford, NJ, and Storm King Art Center. Enjoy scenic river views, a spacious garden, large saltwater pool, and original Beaux-Art details in this architectural gem. *Long stay discounts available (7 days+). Absolutey NO PARTIES/PETS/SMOKING/VAPING!

Private Suite in the Heart of the Hudson Valley

Enjoy a private Croton-on-Hudson suite featuring its own entrance, bathroom, and a striking 6-ft circular window overlooking the trees. This pet-friendly retreat offers a seasonal summer pool, outdoor fire pit, on-site parking, and easy Metro-North transit. Perfectly located near the Hudson River, restaurants, and hiking trails, it serves as the ideal base for daytime exploring and cozy nights. No parties please.

Peaceful & Spacious Home with Pool

Discover the epitome of serenity in this stunning home. Forget your worries in this spacious and serene space. This home is bright, airy, and generously sized. Multiple living rooms and an open-plan kitchen/dining are perfect for spending time with friends and family. Head out back to splash around in the pool, relax by the fire pit, or cook up a feast on the grill.

Matt’s Cozy Quarters Near NYC w/Outdoor Living

Peaceful and beautifully renovated 3BR/2BA home in NY with seasonal pool access (June 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.