Vacation rentals with a pool in Rockland County

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Top-rated rentals with a pool in Rockland County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Home in Peekskill

4.65 out of 5 average rating, 57 reviews

Charming Riverview House at the Inn on the Hudson

Welcome to our newly renovated three-bedroom house, located on the grounds of the Inn on the Hudson, where you can enjoy the best in Hudson Valley hospitality, along with one of the region’s most spectacular Hudson River views. We have space to accommodate 6-10 people, a full kitchen, outdoor patio space, and an outdoor deck overlooking the Hudson River. Take advantage of having your own home with the amenities and services of a boutique hotel, including a seasonal pool and grab & go breakfast!

Guest favorite

Home in Monroe

4.96 out of 5 average rating, 111 reviews

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.

Guest favorite

Camper/RV in Suffern

5 out of 5 average rating, 35 reviews

'54 Stream

40 min. north of Manhattan on the edge of Harriman State Park this unique, fully restored, 1954 Airstream Cruiser 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 private patio, fire pit, and barn. Our inground heated pool is available for guests to enjoy from Memorial Day through Labor Day weekend. Here you can relax and swim after a hike in the woods. Towels provided for pool.

Home in Stony Point

4.86 out of 5 average rating, 76 reviews

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Immerse yourself in a scenic New York haven when you stay at this 2-bedroom, 2-bathroom vacation rental in Stony Point! This stylish home was recently remodeled and features a fully equipped kitchen, an office workspace, and an electric fireplace. Step onto the furnished patio overlooking the on-site stream and soak in the mountain views. Take a dip in the swimming hole on the property, catch some fish in the stocked stream, or just explore the 2 and a half acres surrounded by serene woods!

Guest suite in Croton-on-Hudson

4.61 out of 5 average rating, 76 reviews

Charming Private Suite with views near the Hudson

Bask in the beauty of each season in the Lower Hudson Valley with a giant circular window view! Recently renovated and re-opened, this is a private room and bathroom, with its own separate entrance attached to our single-family home. Quietly nestled on 3 acres of woods and trails, with trains to NYC(44 min ride to Grand Central) and the Hudson Valley only a mile away. We can act as local tour guides for surrounding area, if you have any questions at all. We look forward to hosting you!

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Villa in Monroe

4.85 out of 5 average rating, 20 reviews

Mediterranean Villa

Whether you’re looking for a relaxing getaway or a family trip filled with adventure, you’ll love staying at the ‘Mediterranean Villa’ in the scenic Hudson Valley. Tucked away in Monroe, NY this Villa offers 5-bedrooms, 4-bathrooms, a wood-burning fireplace & enough space for your family to come together and make new memories. Location provides easy access to local attractions: take a day trip to the Catskills, shop locally at the Woodbury Commons or check out the local wineries.

Guest favorite

Home in Monroe

4.85 out of 5 average rating, 47 reviews

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

This exquisite 3-bedroom, 4-bathroom home nestled in the woods of Monroe is just minutes from gorgeous NY state parks, ski resorts, and wineries. This spacious house features modern amenities and magical rustic cabin vibes. Outdoor lovers can explore the large private backyard with a beautiful garden and heated pool. Equipped with elegant living areas, game room entertainment, and an outdoor wraparound deck, guests can enjoy recreation, relaxation, and comfort all vacation long.

Home in Suffern

4.78 out of 5 average rating, 9 reviews

Magical Vacation Paradise

Welcome to the Ultimate Vacation/Party home. Totally Renovated and fully furnished. Everything new and modern. We have the cloud couch! Air bubble hockey, dart board, Pop a Shot Basketball indoors for the kids WIFI and TV's galore Wine cooler Outdoor amenities include: Large backyard and enormous patio Stunning Inground Pool! Outdoor kitchen, Fridge, Ice Maker! BBQ Grill! Putting Green! Fire Pit! Swing Set! Trampoline! BOOK now..... You will have the summer of your dreams!

Guest favorite

Home in Suffern

5 out of 5 average rating, 7 reviews

Spacious w/ Huge Yard, Pool, Fire Pit & Billiards

A tranquil oasis just an hour from NYC, this spacious, elegant home is set on a private, wooded lot with a huge backyard. Take a dip in the sparkling pool, fire up the grill, and dine al fresco on the patio, then gather around the fire pit surrounded by nature for the perfect escape from the day-to-day. Inside, you’ll find upscale furnishings, an enormous kitchen, plenty of places to relax, large flatscreen TVs, a game room with a pool table and, a kids’ reading area, & more.

Guest favorite

Rental unit in Suffern

4.94 out of 5 average rating, 126 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

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Home in Harriman

4.92 out of 5 average rating, 53 reviews

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!

Superhost

Home in Monroe

4.61 out of 5 average rating, 36 reviews

The Sweet Spot: Your Fun-Filled Summer Getaway

Just one hour north of NYC, this large renovated and professionally designed farmhouse is your personal oasis. Enjoy the peace and quiet of the great outdoors, as well as easy access to nearby activities. The Sweet Spot offers tons of entertaining space–both indoors and outdoors– modern and high-end finishes, as well as five bedrooms, an open concept chef’s kitchen and an inground pool on the premises.