Holiday rentals with a pool in Westchester County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Westchester County rentals with a pool

House rentals with a pool

Top Guest favourite
Home in North Salem
4.99 out of 5 average rating, 220 reviews

Converted Barn House

ArthurRating, 5 stars18 months ago
We feel honored to have been Hilary’s last guests. as she has sold the property and is moving away. Hopefully, she will get involved again wherever she ends up because she has a wonderful knack for making people feel at home. Her property was beautiful and we know she will miss it, but I am sure there are great things awaiting her in her new landing spot. Thank you Hilary for such a wonderful stay and good luck to you in the future!!
Guest favourite
Home in Ossining
5 out of 5 average rating, 14 reviews

Pool/HotTub - Close to NYC

CynthiaRating, 5 stars6 months ago
Nice location, easy transit! Good value.
Home in Katonah
4.8 out of 5 average rating, 5 reviews

Luxury 4 bedroom Modern Barn with Pool

ThomasRating, 5 stars9 months ago
Our stay at this unique home was fantastic! The 5 acres of beautiful land provided a perfect backdrop for relaxation and fun. The kids especially loved the pool and spent hours playing in it. The downstairs play area with a ping pong table was a big hit too. The open layout of the house was perfect for family time, and the large deck was ideal for outdoor meals and cozy evenings. The bedrooms were comfortable, and the extra sleeping spaces were a great addition. A highlight of our stay was the chickens. The kids had a blast collecting fresh eggs every morning. Overall, this home exceeded our expectations and provided an great experience.
Top Guest favourite
Home in Highland Falls
5 out of 5 average rating, 13 reviews

Billy Joel/JP Morgan Hudson Valley Home 1h to NYC

KevinRating, 5 stars2 weeks ago
The house and property are truly amazing. Located on the Hudson River with beautiful views and peaceful surroundings. We did not hear or notice any neighbors. The back area is completely private. This house is so spacious and we had plenty of room for a family get together, hosting 18 people for dinner. The kitchen is fully equipped with all that we needed, with all new beautiful dishes, glassware and serving platters. The linens and towels were crisp white…all seem to be brand new. This historic house has lots of charm with antique and new furnishings, as well as local interest items on the shelves and walls. The gas fireplace worked perfectly and was a great touch to the house. Benjamin was above and beyond a great host. His response time was literally just a few minutes. He was very helpful with any requests and went out of his way to make us feel welcome and comfortable. We highly recommend this property and will love it if we get a chance to return.
Guest favourite
Home in Greenwich
4.97 out of 5 average rating, 39 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

HangRating, 5 stars2 months ago
This house has a river view which I liked the most. Because the land is so big, I feel I am in a forest next to a river with quiet and private environment. The owner is great and responded in no time. I will refer to my friends.
Home in Wilton
4.6 out of 5 average rating, 10 reviews

Poolside Paradise: Luxe 5-Bedroom w/Peloton Gym

ChristineRating, 5 stars30 months ago
Incredible space inside and out. The area is gorgeous, near charming Ridgefield, Wilton and New Canaan town centers. Our family of 7 stayed here and the house had more than enough space. Fun large bonus room with ping pong table, outside fire pit and two generous living rooms gave us lots of room. We really enjoyed ourselves.
Home in South Salem
4.88 out of 5 average rating, 16 reviews

Lakefront w/ Pool, Dock, & Lake Sunset Views

HeatherRating, 5 stars20 months ago
It’s a beautiful, beautifully maintained home with gorgeous landscaping and marvelous pool. Everything is easy and comfortable. Everything is clean. Towels and linens are nice. Neighbors are super close, but the landscaping makes you feel like you are in a secluded place. The property manager got back to my questions in minutes—always very, very nice and totally helpful. Only negative thing I can say is that the storage shed by the lake front (where extra chairs are, oars for row boat, etc.) and the things in it are neglected.
Home in Yorktown Heights
4.89 out of 5 average rating, 9 reviews

* Overlook the Reservoirs Custom Victorian Farmhse

TimothyRating, 5 stars3 months ago
We had an incredible stay at this beautiful home for the holidays! The house is spacious and immaculately decorated, with thoughtful touches that made it feel warm and inviting. The layout was perfect for hosting our family gatherings, with plenty of room for everyone to spread out and relax. The kitchen was fully equipped, making meal prep a breeze, and the cozy living areas were ideal for relaxing.. The quiet suburban setting offered a peaceful retreat, while still being close to everything we needed. We couldn’t have asked for a better place to create lasting holiday memories. Highly recommend!

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