
Vacation rentals in Pleasantville
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Top-rated vacation rentals in Pleasantville
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Pleasantville vacation rentals
Other great vacation rentals in Pleasantville
Top guest favorite

Home in Valhalla
5 out of 5 average rating, 15 reviewsValhalla Home
MichaelRating, 5 stars5 days ago
A perfect spot for visiting Westchester. Easy access to the City and easy access to Tarrytown etc... The place was great. A big space in a super cool 50s era house with super modern amenities.

Guest suite in Pleasantville
4.65 out of 5 average rating, 57 reviewsEntire Pleasant Private Studio APT
MarkRating, 5 stars8 months ago
Sue’s unit was the perfect place for me to stay for a weekend wedding in the town center of Pleasantville. Very convenient parking and access, clear instructions, and great communication. Nice bed and bathroom. Easy walk into town, especially nice with the turning leaves.
Guest favorite

Apartment in Valhalla
4.86 out of 5 average rating, 22 reviewsSpacious 1 bedroom close to town, airport, train
Sarah and AaronRating, 5 stars8 months ago
Perfect for what we needed. Debra was a great host. Would definitely book again. Made traveling in the area super easy. Had a great off street parking spot, right next to door. No stairs, easy in and out.

Apartment in Piermont
4.73 out of 5 average rating, 60 reviewsCozy Piermont Cottage
BruceRating, 5 stars2 weeks ago
Thank you Rachel your place is perfect for a visit w family and friends. I love the space and location. I’ll be back.
Guest favorite

Guesthouse in Chappaqua
4.95 out of 5 average rating, 87 reviewsCozy 2 Bedroom Cottage in Stunning Setting
CandiceRating, 5 stars2 weeks ago
Tamara's place was perfect for what we needed! She was very communicative and easy to work with!
Guest favorite

Apartment in Ossining
4.87 out of 5 average rating, 15 reviewsThe Yellow Brick Getaway
NadiaRating, 5 stars2 weeks ago
Enjoyed our stay and found Melita very helpful, friendly and proactive with advice. We had hired a car and needed parking permit and she took care of getting the required permit as well as taking care of the parking fine we received due to our misunderstanding of the conditions. Thank you Melita.
Top guest favorite

Guest suite in Putnam Valley
4.99 out of 5 average rating, 120 reviewsNestled in Nature
LindseyRating, 5 stars5 days ago
Our stay here was wonderful! Clean, welcoming, and Justin was extremely kind. My young boys loved the dog, goats, and pond! Everything you could need or want was there. Bedroom was spacious enough to fit a pack-n-play for our youngest and both beds were comfortable. Would definitely stay again!
Guest favorite

Guest suite in Haverstraw
4.86 out of 5 average rating, 69 reviewsUnique comfortable guest suite
JonathanRating, 5 stars2 weeks ago
Maria’s listing was a cozy step up, clean and had everything I needed over the 4 days of my stay! Maria was quick to respond to any questions or concerns I had and was able to provide clear instructions on how to check in and check out of the apt.
Quick stats about vacation rentals in Pleasantville
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
660 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Self check-in, Gym, and BBQ grill
Local attractions
Wood & Fire, Southern Table kitchen & Bar, and The Pleasantville Diner
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo