Vacation 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!!
Top guest favourite
Home in Wilton
5 out of 5 average rating, 19 reviews

Historic 3 Acre Estate | Pool+HotTub | Firepit+BBQ

ElizabethRating, 5 stars6 months ago
We were blown away with the history and charm of this home. With all updated amenities, the owners were able to keep the history flowing through every room. Just 7 minutes from downtown Ridgefield it was the perfect location to stay with extended family and still be part of all the fun Ridgefield has to offer.
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.
Guest favourite
Home in Greenwich
4.98 out of 5 average rating, 40 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

YiqiaoRating, 5 stars2 months ago
I booked this for my parents. They absolutely loved it. They enjoyed the snow and the place looks beautiful! It is definitely a great stay and we will deficiencies back! The host is super helpful and responsive!
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

1 hr from NYC: Custom Victorian Farmhse

TimothyRating, 5 stars4 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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