Top 10 Airbnbs With Pool In Westchester County, New York


From busy cities to scenic towns, Westchester County offers unique experiences that will make your vacation memorable. Situated in Hudson Valley, the county is home to historically important destinations, including Kykuit, the Rockefeller Estate, Broadway, and Lyndhurst Mansion. It also has plenty of gardens and parks where you can appreciate nature and architecture. These include Untermyer Gardens Conservancy and Rockefeller State Park Preserve. Of course, the area also has places for shopping, entertainment, and outdoor adventures. Some of the favorite tourist spots are LEGOLAND Discovery Center Westchester, Ridge Hill, and Croton Gorge Park.

When it comes to traveling, accommodation should also be your main concern. You will want to stay somewhere with relaxing amenities after all the activities you’ve done. As such, check out these top Airbnbs with pool in Westchester County, New York.

1. The Westchester Castle, Ossining (from USD 686)

Feel like a VIP when you stay in this majestic home in Ossining, New York. It’s the perfect place for honeymooners and families of travelers. It has a private outdoor pool that is open from spring until early fall. Here, you can take a dip and relax while admiring the picturesque mountain and golf course views.

Thanks to a fully equipped kitchen, a washer and dryer, and a fast WiFi connection, you’ll have everything you need for a convenient stay. Moreover, the place also has a smart TV with Netflix, HBO Max, and Hulu, to keep you entertained throughout your vacation.

Luxurious 7BR w/ Heating & Pool!
Ossining, New York, United States
60 reviews  Wifi Available
Entire home 9 Beds 13 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 13

Top guest reviews
Amenities & Room:
both occupants were friendly and the pool was only accessible to us
everything was clean and organized
it was clean quiet and safe
the hosts were fantastic and super responsive
the owners were very accommodating and helpful if we ever needed anything
it was close to everything and we enjoyed our saturday night in playing pool and watching movies
Read more reviews

2. Rustic barn house with a private balcony, North Salem (from USD 260)

If you love art and decorations, then you will be amazed by the details of this converted barn house. Every nook and cranny is adorned with pieces of art and decor to create a warm and homey ambiance. Even the outdoors is also admirable, especially the 100-year-old outdoor bathtub and the private pool that is open 24 hours a day from January to November. Pool toys will be available too.

Right by the water, you will find an underground stone firepit that you can light up at night. If you are not swimming or exploring North Salem, you can just unwind on the patio or play ping-pong or pool.

Converted Barn House
North Salem, New York, United States
188 reviews Superhost  Wifi Available
Entire home 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the yard and the pool are just amazing
a literal oasis the barn is absolutely stunning so comfortable and well decorated
the space is very comfortable and charming we hope to be back again soon :)
we hope to return when the weather warms and enjoy the pool and the outdoor space
the pool outdoor shower indoor/outdoor fireplaces are just some of the wonderful aspects of hilary's property
the barn itself was spotless and charming
the place was extremely clean and the pool was amazing
the barn is gorgeous clean cozy and truly special
her barn is beautiful and clean and furnished with everything you might need
her property is very clean and the listing description is very accurate
hillary is a great host
hilary is a thoughtful host
hilary was an amazing host and was so kind
she is attentive to every detail and a very nice person
hilary is also the most communicative generous host
a wonderful location stylish and well organized
we enjoyed the location because it was a great getaway from the city life
i would recommend the location to anyone that is looking for serenity
there’s also a little market within walking distance that has delicious pastries for breakfast
great location and a fantastic host
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3. Cozy apartment with dedicated workspaces, White Plains (from USD 151)

Working while traveling? This apartment in White Plains will be the right choice for you. It features spacious workspaces with scenic views, allowing you to focus on your job even though you are away. It also has an outdoor pool that is open 24 hours a day so that you can go for a dip or do a lap anytime. The pool availability is from January to September.

With plenty of outdoor space, kids can run around and play. You can also have a barbecue here.

An escape close to cities! Seasonal outdoor pool
White Plains, New York, United States
6 reviews  Wifi Available
Entire home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
spacious clean quiet and well appointed
Read more reviews

4. Labrador Manor, Port Chester (from USD 925)

Built-in 1916, Labrador Manor provides visitors of Port Chester with a rustic stay. Aside from its charming interior design, you will also love its outdoor features. It has a private swimming pool with luxurious landscaping and a waterfall feature. You and your group are going to spend a lot of time in the pool area, swimming or lying on the surrounding sun loungers. Here, you will also have access to a private patio where you can see the horticultural handiwork of the owners.

Additionally, this pet-friendly house is just 10 minutes from a beach where you can watch the sunrise.

Labrador Manor: Westchester County Home with Pool
Port Chester, New York, United States
7 reviews Superhost  Wifi Available
Entire home 3 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the outdoor space is beautifully landscaped with a large amazing swimming pool deck chairs propane grill etc
the kitchen is huge and very well equipped with cooking tools and a drawer full of spices
colleen is a wonderful host
colleen is a generous host and provided lots of recommendations and was quick to respond to questions
great house great host thank you
extremely accommodating and kind
this was a perfect location and home for our family of 4 - 2 adults and 10yo twins
Read more reviews

5. Charming poolhouse with garden views, Briarcliff Manor (from USD 375)

Looking for a place to cool off and relax? Bring your family or group of friends to this cozy poolhouse in Briarcliff Manor. You will have approximately 2 acres (0.81 hectares) of private woodland gardens to enjoy all by yourself. For a truly rejuvenating time off, this accommodation features a heated outdoor pool surrounded by natural beauty.

It also has a hot tub where you can soak while sipping your favorite beverage. Relish the outdoors at night by dining alfresco or having a barbeque dinner by the pool.

Poolhouse paradise on private grounds close to NYC
Briarcliff Manor, New York, United States
6 reviews  Wifi Available
Entire bungalow 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the pool had a number of inflatables as well
we had a lovely stay in laura’s clean beautifully decorated kid-friendly pool house
laura was very responsive to my needs and a very gracious host
Read more reviews

6. Secluded rental with modern amenities, Carmel Hamlet (from USD 496)

Escape the hustle and bustle to experience tranquility in this private home in the woods. Tucked away on quiet and private land, it offers a variety of amenities to keep your stay comfortable and fun. Its inground outdoor pool is 36 feet (10.97 meters) by 20 feet (6.10 meters), making it large enough to accommodate many guests. Beside it, you’ll find a spacious lounge area where you can relax in the shade.

The pool is available seasonally from 9am to 8pm from June to September. Meanwhile, the 7-person hot tub is open 24 hours a day all year.

Cozy Winter Getaway with hot tub
Carmel Hamlet, New York, United States
45 reviews Superhost  Wifi Available
Entire home 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
our favorite room was the beautiful dining room overlooking the deck and the backyard
our children found even the toilet with the bidet exciting
the pool the hot tub the kitchen and the master bedroom are amazing
of course the master bathroom felt like being in a spa
from the sound system to the gorgeous pool the hot tub to the games
it is very clean and comfortable quiet and beautiful and has everything you could need
the place was in terrific shape-- super clean with comfortable bedding
the pool was so refreshing and clean
the house is great - well appointed clean and perfect for an escape would definitely recommend and stay again
it is one of those places that you hope lasts forever and everyone keeps clean and truly appreciates
the host was super responsive
hosts are super nice and friendly
calum was a great host
thank you callum and lillian for being such amazing hosts
the area is beautiful the property is fantastic to explore and the host is very kind and responsive
very close to several cute orchards
beautiful property in a nice location
incredibly close to the city easy automatic check-in good grocery stores around
the house is conveniently located close to nyc and overall great
an amazing place to get away from it all
Read more reviews

7. Serene private suite in an upscale neighborhood, Rye (from USD 168)

This private suite is a perfect choice for expatriates, business travelers, and small families. It is safe, secure, and conveniently located close to restaurants, historical landmarks, and other tourist spots. You will enjoy your vacation even if you don’t go out by relaxing in the heated outdoor pool that features a beautiful natural landscape.

The pool is 10 feet (3.05 meters) deep and is suitable for diving. Guests will be free to use the diving board and water toys when the pool is open from May to September. There are also private beaches just a few minutes’ walk from the property.

Serene Private Oasis in Rye: Tranquility Suite
Rye, New York, United States
247 reviews  Wifi Available
Private room in home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
he loved the cozy extra soft bed and of course the pool
the suit has a comfortable bed and sofa a good size to host two people comfortably
the bed was extremely comfortable
the room is quaint with comfortable bed albeit full size so rather tight for couples
the apartment was nice and cozy and a great location near downtown port chester and the capitol theatre
very clean and cozy room
very clean and comfortable
room is very clean and quiet and the neighborhood is quite beautiful
the pool was clean and huge plenty of space to do a few laps
host is very friendly and helpful
the host is super nice and understanding
great stay and great host
franklin is an excellent host
very accommodating and helpful to any questions we had
location was great for me
location was perfect for our purposes
great house in a great location and fantastic hosts
i hope to return to franklin's place next summer while revisiting westchester county
location was great and his place was perfect for the two of us
Read more reviews

8. Colonial farmhouse with gorgeous pond, Yorktown Heights (from USD 600)

Are you in Yorktown Heights for a vacation? Book a stay in this lovely colonial farmhouse. The place looks and feels like a sanctuary thanks to its wood-burning fireplace, thriving garden, and well-equipped kitchen.

It also has an outdoor swimming pool that overlooks scenic rolling landscapes. The pool is heated to keep you warm and comfy in the water. Aside from this, another remarkable feature of the house is a private pond where you can find a rowboat. The gazebo will be a peaceful place to rest, but you can also paddle across the pond to better admire the natural surroundings.

Comfort and Tranquility awaits for you !!
Yorktown Heights, New York, United States
85 reviews Superhost  Wifi Available
Entire home 4 Beds 8 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
there were also fresh flowers in every room
but our favorite spot was the wonderful heated pool
we had an issue with the water heater and dani was very quick to help resolve the problem
the evenings we are watching movies and our morning breakfasts are amazing with the flat top griddle
the house is so spacious we really had room to spread out and relax
the house was clean spacious and well maintained
the house is spacious and extremely clean
rooms are comfortable and place is very clean
the pool was lovely and clean surrounded by trees and nature (we spotted deer )
wonderful place and great host
dani was such a gracious host
dani is very responsive in answering questions and troubleshooting
dani was a very responsive host
dani was an excellent host for our family
the house is beautiful and is in a great location
dani’s place is in a perfect location secluded in the woods with lots of privacy
the yard was fun and we were in a great location to explore nearby attractions
the house pool and location are perfect for those looking for a little r and r
this house is definitely the perfect place to stay in yorktown heights
Read more reviews

9. Stunning villa with vintage-style details, Irvington (from USD 4143)

Since several films and series have been shot in Villa Nuits, staying here will surely make you feel like you are a character from a period movie. There are a lot of great things to love about this historical estate, and its spacious outdoor pool area is one of them.

The property features a heated inground pool where guests can swim and play in addition to a hot tub. It also has plenty of sun loungers and seating space, making it a spectacular place to unwind with your loved ones.

Villa Nuits (nuitsonhudson) 30 mins to NYC!
Irvington, New York, United States
42 reviews  Wifi Available
Entire villa 19 Beds 16 Guests 13 Bedrooms 10 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
it’s a giant old mansion with lots of great amenities beautiful grounds and a terrific pool
the photos can't do it justice- it is just magnificent room after magnificent room of stunning craftsmanship
our group will definitely be back in the summer when the pools open
if you're looking to have an outdoor gathering at the pool be sure to inquire
guest rooms are furnished with quality bedding and comfortable seating areas
lots of clean towels fully stocked kitchen beautiful fireplace etc
martin was a fantastic host
the owner and his crew are friendly and helpful
martin the host was great in responding in a timely manner to any questions i had
martin is a friendly communicative host and all around class act
martin was very responsive and accommodating
great location with a short walk to the train station and beautiful views throughout
it's a great location and there is great history with the house
the location couldn’t be more perfect and the house itself is spectacular
i would highly recommend this home for an unforgettable intimate event or a location for a production
the house was clean and comfortable great location very recommended
Read more reviews

10. Serene villa with picturesque garden views, New Rochelle (from USD 1000)

Looking for a place to spend your summer in New Rochelle? Choose this family-friendly accommodation. When you are not out and about, you will be free to rest and play in the outdoor pool area. While it is not heated, it will still be great for swimming, floating, and keeping you cool on hot days. Do check with the host beforehand to ensure it will be open during your visit.

The outdoors also offers plenty of space for kids to run around and play. In fact, the backyard has swings and a slide. With outdoor furniture and a grill, dining alfresco will be fun.

7 BR, 5 BA: 15 Miles to Midtown NYC (Private Pool)
New Rochelle, New York, United States
22 reviews  Wifi Available
Entire villa 8 Beds 12 Guests 7 Bedrooms 5 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
plenty of space air conditioned rooms and a great deck with bbq included
we loved the pool deck and public areas for relaxing
the house is spacious and comfortable and had all amenities we could've needed
the deck was amazing and we wished it was warm enough to use the pool
the pool large yard and large covered patio are perfect places to spend the long summer days
the house was very clean and prepared for our arrival
our hosts are lovely people available for questions with prompt and helpful responses
scott was a great host
scott and emmy were excellent hosts
scott was an excellent host who went above and beyond to make our stay perfect
he was very responsive and even sent a text to check in during our stay
great for kids close to parks
you are super close to nyc without the nyc noise which is a huge plus
pictures do not do this place justice scott's home is beautiful and located in a gorgeous neighborhood
Read more reviews

Experience a relaxing vacation you deserve in Westchester County

Airbnbs with pools will provide guests with more ways to unwind after a tiring tour around Westchester County. They also offer a fun place to bond with families or friends. For a relaxing and memorable getaway, book a stay at one of the top-notch accommodations above.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Hello, I am Kriselle. I am a content writer from the Philippines who loves to share her experiences and adventures through blogging. I'm a fur mom who likes to travel and discover off-the-beaten...Read more

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