Vacation rentals with a pool in Rockland County

Find and book unique homes with a pool on Airbnb

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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Guest favorite

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Jan 27 – Feb 3

G$167,696 GYD per night

Guest favorite

Home in Middletown

4.94 out of 5 average rating, 100 reviews

Springtime farm escape with hot tub and amenities

Looking for a perfect Winter upstate retreat? Look no further! Welcome to our beautiful 100 year old farmhouse! Nestled on over two acres in the Southern valley of the Shawangunk mountains, this is a beautiful area to explore foliage and hikes, stay home to soak in the hot tub, warm up by the fireplace, or cook! We are located in the Sullivan County Catskill region, next to the Hudson Valley and Delaware River regions. With farmland and hiking nearby, we know you will love this beautiful area.

Dec 26 – Jan 2

G$60,416 GYD per night

Guest favorite

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 94 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Set in historic 1750's farmhouse, located in the center of Teatown Lake Reservation with over 1,000 acres of trails in our backyard, this elegant getaway has all the luxuries of a resort (pool, cedar barrel sauna, spa tub, rain shower) while maintaining the rustic charm of a working farm. Easily accessible to NYC, yet worlds away-- a chic private refuge where you can unwind and restore to the gentle sounds of nature (& the occasional rooster.) Friendly dogs and artists:) Sorry, no kids or pets.

Aug 24 – 31

G$46,674 GYD per night

Guest favorite

Home in West Milford

4.99 out of 5 average rating, 113 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Aug 22 – 29

G$85,460 GYD per night

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Oct 26 – Nov 2

G$115,420 GYD per night

Guest favorite

Apartment in Wappingers Falls

5.0 out of 5 average rating, 174 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom.

Jun 22 – 29

G$42,963 GYD per night

Superhost

Home in Yorktown Heights

4.88 out of 5 average rating, 119 reviews

Cozy winter getaway 1 hr from NYC!

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

Sep 19 – 26

G$70,932 GYD per night

Guest favorite

Apartment in Chester

5.0 out of 5 average rating, 16 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Nov 23 – 30

G$27,689 GYD per night

Guest favorite

Apartment in Suffern

4.95 out of 5 average rating, 105 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.

Jul 23 – 30

G$33,755 GYD per night

Guest favorite

Home in Englewood

4.94 out of 5 average rating, 131 reviews

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!

Oct 22 – 29

G$94,492 GYD per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 394 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Apr 15 – 22

G$19,047 GYD per night

Guest favorite

Guest suite in Holmes

4.98 out of 5 average rating, 165 reviews

Pool opens 5/24! Huge & Eclectic 1.5 hr to NYC!

1.5 hrs from NYC; minutes driving from hiking trails; 20 min from Beacon and Cold Spring! The bottom floor of this 1865 Carriage House has been transformed into an eclectic retreat. The 2500 sq ft private apartment has a room for every mood and super unique decor in every corner! There is also a vintage/antique shop on the property— 20% off for our guests ;)

Nov 20 – 27

G$45,234 GYD per night