
Holiday rentals with a pool in Westchester County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westchester County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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House rentals with a pool
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Home in Port Chester
5 out of 5 average rating, 11 reviewsLabrador Manor: Westchester County Home with Pool
BlakeRating, 5 stars7 months ago
Colleen’s place is beautiful and exactly as advertised. We had no issues and she was very communicative leading up to our stay to make it easy.
Top Guest favourite

Home in North Salem
4.99 out of 5 average rating, 220 reviewsConverted Barn House
ArthurRating, 5 stars17 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 Stamford
4.98 out of 5 average rating, 56 reviewsGameroom, backyard + pool! 7m to train + downtown
ScottRating, 5 stars1 month ago
We really enjoyed our stay at Ya & Diego's home. It was even nicer than it looked in the pictures and the location was perfect. We were able to get downtown within 8 minutes, Harbor Point was only approximately 10 - 12 minutes, and the new Whole Foods market was 1/2 mile away, so it was very convenient. Diego was extremely responsive before, during, and after our trip. We look forward to visiting again this summer to enjoy the yard and pool which will make the stay even nicer!
Guest favourite

Home in Ossining
5 out of 5 average rating, 14 reviewsPool/HotTub - Close to NYC
CynthiaRating, 5 stars5 months ago
Nice location, easy transit! Good value.

Home in Katonah
4.8 out of 5 average rating, 5 reviewsLuxury 4 bedroom Modern Barn with Pool
ThomasRating, 5 stars8 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 Carmel Hamlet
4.93 out of 5 average rating, 73 reviewsCountry getaway with hot tub on 9 acres
VinnyRating, 5 stars2 months ago
We loved our stay in Calum's Airbnb! It is a short commute from NYC and conveniently located between two main areas with plenty of grocery store and restaurant options. The home itself is well equipped with an amazing kitchen and many board games - so we were always entertained.

Home in Waccabuc
5 out of 5 average rating, 3 reviewsLakefront home with multiple bedrooms, indoor and outdoor entertaining areas.
DanielRating, 5 stars20 months ago
We really enjoyed our stay at Beth's! It was so peaceful and wonderful to be right on the lake but also to have a pool! Our family is nearby, so we will def book again when we visit!
Guest favourite

Home in Greenwich
4.97 out of 5 average rating, 39 reviewsRiverfront 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.
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