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 StatesAccommodates: 13
Top guest reviews
Amenities & Room:
both occupants were friendly and the pool was only accessible to usHost:
the hosts were fantastic and super responsivethe owners were very accommodating and helpful if we ever needed anythingRead more reviewsLocation:
it was close to everything and we enjoyed our saturday night in playing pool and watching movies
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 HouseNorth Salem, New York, United StatesSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
the yard and the pool are just amazinga literal oasis the barn is absolutely stunning so comfortable and well decoratedthe 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 spacethe pool outdoor shower indoor/outdoor fireplaces are just some of the wonderful aspects of hilary's propertyCleanliness:
the barn itself was spotless and charmingthe place was extremely clean and the pool was amazingthe barn is gorgeous clean cozy and truly specialher barn is beautiful and clean and furnished with everything you might needher property is very clean and the listing description is very accurateHost:
hillary is a great hosthilary is a thoughtful hosthilary was an amazing host and was so kindshe is attentive to every detail and a very nice personhilary is also the most communicative generous hostRead more reviewsLocation:
a wonderful location stylish and well organizedwe enjoyed the location because it was a great getaway from the city lifei would recommend the location to anyone that is looking for serenitythere’s also a little market within walking distance that has delicious pastries for breakfastgreat location and a fantastic host
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 poolWhite Plains, New York, United StatesAccommodates: 2
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 PoolPort Chester, New York, United StatesAccommodates: 8
Top guest reviews
Amenities & Room:
the outdoor space is beautifully landscaped with a large amazing swimming pool deck chairs propane grill etcthe kitchen is huge and very well equipped with cooking tools and a drawer full of spicesHost:
colleen is a wonderful hostcolleen is a generous host and provided lots of recommendations and was quick to respond to questionsgreat house great host thank youextremely accommodating and kindRead more reviewsLocation:
this was a perfect location and home for our family of 4 - 2 adults and 10yo twins
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 NYCBriarcliff Manor, New York, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
the pool had a number of inflatables as wellCleanliness:
we had a lovely stay in laura’s clean beautifully decorated kid-friendly pool houseRead more reviewsHost:
laura was very responsive to my needs and a very gracious host
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 tubCarmel Hamlet, New York, United StatesAccommodates: 8
Top guest reviews
Amenities & Room:
our favorite room was the beautiful dining room overlooking the deck and the backyardour children found even the toilet with the bidet excitingthe pool the hot tub the kitchen and the master bedroom are amazingof course the master bathroom felt like being in a spafrom the sound system to the gorgeous pool the hot tub to the gamesCleanliness:
it is very clean and comfortable quiet and beautiful and has everything you could needthe place was in terrific shape-- super clean with comfortable beddingthe pool was so refreshing and cleanthe house is great - well appointed clean and perfect for an escape would definitely recommend and stay againit is one of those places that you hope lasts forever and everyone keeps clean and truly appreciatesHost:
the host was super responsivehosts are super nice and friendlycalum was a great hostthank you callum and lillian for being such amazing hoststhe area is beautiful the property is fantastic to explore and the host is very kind and responsiveRead more reviewsLocation:
very close to several cute orchardsbeautiful property in a nice locationincredibly close to the city easy automatic check-in good grocery stores aroundthe house is conveniently located close to nyc and overall greatan amazing place to get away from it all
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 SuiteRye, New York, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
he loved the cozy extra soft bed and of course the poolthe suit has a comfortable bed and sofa a good size to host two people comfortablythe bed was extremely comfortablethe room is quaint with comfortable bed albeit full size so rather tight for couplesthe apartment was nice and cozy and a great location near downtown port chester and the capitol theatreCleanliness:
very clean and cozy roomvery clean and comfortableroom is very clean and quiet and the neighborhood is quite beautifulthe pool was clean and huge plenty of space to do a few lapsHost:
host is very friendly and helpfulthe host is super nice and understandinggreat stay and great hostfranklin is an excellent hostvery accommodating and helpful to any questions we hadRead more reviewsLocation:
location was great for melocation was perfect for our purposesgreat house in a great location and fantastic hostsi hope to return to franklin's place next summer while revisiting westchester countylocation was great and his place was perfect for the two of us
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 StatesAccommodates: 8
Top guest reviews
Amenities & Room:
there were also fresh flowers in every roombut our favorite spot was the wonderful heated poolwe had an issue with the water heater and dani was very quick to help resolve the problemthe evenings we are watching movies and our morning breakfasts are amazing with the flat top griddlethe house is so spacious we really had room to spread out and relaxCleanliness:
the house was clean spacious and well maintainedthe house is spacious and extremely cleanrooms are comfortable and place is very cleanthe pool was lovely and clean surrounded by trees and nature (we spotted deer )Host:
wonderful place and great hostdani was such a gracious hostdani is very responsive in answering questions and troubleshootingdani was a very responsive hostdani was an excellent host for our familyRead more reviewsLocation:
the house is beautiful and is in a great locationdani’s place is in a perfect location secluded in the woods with lots of privacythe yard was fun and we were in a great location to explore nearby attractionsthe house pool and location are perfect for those looking for a little r and rthis house is definitely the perfect place to stay in yorktown heights
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 StatesAccommodates: 16
Top guest reviews
Amenities & Room:
it’s a giant old mansion with lots of great amenities beautiful grounds and a terrific poolthe photos can't do it justice- it is just magnificent room after magnificent room of stunning craftsmanshipour group will definitely be back in the summer when the pools openif you're looking to have an outdoor gathering at the pool be sure to inquireguest rooms are furnished with quality bedding and comfortable seating areasCleanliness:
lots of clean towels fully stocked kitchen beautiful fireplace etcHost:
martin was a fantastic hostthe owner and his crew are friendly and helpfulmartin the host was great in responding in a timely manner to any questions i hadmartin is a friendly communicative host and all around class actmartin was very responsive and accommodatingRead more reviewsLocation:
great location with a short walk to the train station and beautiful views throughoutit's a great location and there is great history with the housethe location couldn’t be more perfect and the house itself is spectaculari would highly recommend this home for an unforgettable intimate event or a location for a productionthe house was clean and comfortable great location very recommended
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 StatesAccommodates: 12
Top guest reviews
Amenities & Room:
plenty of space air conditioned rooms and a great deck with bbq includedwe loved the pool deck and public areas for relaxingthe house is spacious and comfortable and had all amenities we could've neededthe deck was amazing and we wished it was warm enough to use the poolthe pool large yard and large covered patio are perfect places to spend the long summer daysCleanliness:
the house was very clean and prepared for our arrivalHost:
our hosts are lovely people available for questions with prompt and helpful responsesscott was a great hostscott and emmy were excellent hostsscott was an excellent host who went above and beyond to make our stay perfecthe was very responsive and even sent a text to check in during our stayRead more reviewsLocation:
great for kids close to parksyou are super close to nyc without the nyc noise which is a huge pluspictures do not do this place justice scott's home is beautiful and located in a gorgeous neighborhood
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.
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to bookmark our articles, like local expert tips, receive great stories in your inbox, and follow writers and topics that you love.
Log in with Facebook Log in with Twitter Log in with Google ×