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Vacation rentals with a pool in Westchester County

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Top-rated rentals with a pool in Westchester County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Superhost
Home in Yorktown Heights
Cozy winter getaway 1 hr from NYC!
This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, a huge DECK, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & crib. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.
Jun 24 – Jul 1
$663 per night
4.88 out of 5 average rating, 112 reviews
Guest favorite
Apartment in Rye Brook
Cozy studio near Port Chester.
Studio basement apartment ( walk out ), individual entrance, private parking, 1 mile from the capitol theater in Port Chester, 35 minutes train ride to Grand central terminal, quiet neighborhood and very private. Please note that the outside area with pool and jacuzzi is open ONLY during the summer months. No parties or events allowed. Family home, you will have access to the entire basement apartment with individual entrance. We only accept guests with positive past reviews.
Jul 25 – Aug 1
$117 per night
4.86 out of 5 average rating, 7 reviews
Guest favorite
Home in Stamford
Midcentury Modern ZenHouse Sculptor Studio
Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio
Mar 7 – 14
$272 per night
4.97 out of 5 average rating, 215 reviews

Popular amenities for Westchester County rentals with a pool

House rentals with a pool

Guest favorite
Home in Bedford
The Waterside Guest House with Pool & Tennis, Golf
Feb 10 – 17
$854 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Greenwich
Retreat w/pool/Free Parking/Fireplace /Downtown
Mar 18 – 25
$254 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Yonkers
Entire home- pool, gym, theater. 10 min from NYC.
Jun 29 – Jul 6
$583 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Stamford
Gameroom, backyard + pool! 7m to train + downtown
Aug 17 – 24
$616 per night
5.0 out of 5 average rating, 34 reviews
Guest favorite
Home in Yonkers
Beautiful home w/ outdoor space +Pool
Sep 3 – 10
$524 per night
4.97 out of 5 average rating, 32 reviews
Guest favorite
Home in Katonah
Contemporary Retreat w/ GameRoom Fireplace HBO
May 25 – Jun 1
$431 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Wilton
Historic 3 Acre Estate | Pool+HotTub | Firepit+BBQ
Jun 4 – 11
$694 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Carmel Hamlet
Country getaway w/ hot tub & Fireplace on 9acres
Jun 7 – 14
$578 per night
4.92 out of 5 average rating, 64 reviews
Guest favorite
Home in Philipstown
Modern Cottage in the Woods, Garrison
May 7 – 14
$389 per night
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Stamford
Stamford Serenity |PondSide Haven|3 Beds|2.5 Baths
Sep 29 – Oct 6
$154 per night
4.75 out of 5 average rating, 4 reviews
Guest favorite
Home in Port Chester
Labrador Manor: Westchester County Home with Pool
Jun 6 – 13
$925 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Mahopac
Heated Pool | Hot Tub | Fire Pit | Backyard Oasis
Jul 12 – 19
$747 per night
5.0 out of 5 average rating, 15 reviews

Destinations to explore