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

Superhost
Home in Port Chester
5 out of 5 average rating, 11 reviews

Labrador 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.
Guest favourite
Home in Stamford
4.98 out of 5 average rating, 56 reviews

Gameroom, 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 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 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 reviews

Country getaway with pool and 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 reviews

Lakefront 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 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.

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