Search Vacation Homes in Pleasantville

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 276 Vacation Homes in Pleasantville with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (9)
"This was amazing Thanksgiving with my family. The house is amazing Jon was amazing host and his recommendation for food made you feel like million dollars. Can not thank you enough to share your beautiful home with us and see you in the summer."
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

9.6 out of 10, Exceptional, (47)
"Awesome amenties, great neighborhood and very friendly and accomodating host."
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

9.4 out of 10, Exceptional, (8)
"Great place for a group of friends to use as homebase for some shows at the Capitol Theater. "
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (16)
"The house is beautiful, amazing views! Communication was punctual."
The price is AED 1,208
AED 2,864 total
includes taxes & fees
23 Dec - 24 Dec
Waterview House Walking Distance from Cove Beach

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
The price is AED 2,575
AED 4,615 total
includes taxes & fees
2 Jan - 3 January 2025
New Beach Home near Stamford Downtown/Shippan

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!

10.0 out of 10, Exceptional, (7)
"Everything was great"
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!

Up-to-date Home w/ Pool, Playground & Fireplace!

Up-to-date Home w/ Pool, Playground & Fireplace!

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"Second time our 24 person family group stayed here, and if anything, it was even better than last year! The location is exceptional, a quiet, private beautiful Victorian era house right on the Sound. The house is roomy, immaculate and very well equipped. Nancy is on top of everything and responds essentially immediately to any and every concern. There aren’t enough superlatives to describe our wonderful experience! "
Waterfront Retreat Center for Health & Wellness

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (21)
"Long weekend with family to participate in a christening in the Bronx. Place was clean and comfortable. Location was very convenient. Only change I would request would be extra blankets. Otherwise would stay again. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is AED 918
AED 1,374 total
includes taxes & fees
8 Jan - 9 January 2025
Contemporary Cozy Cottage

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is AED 999
AED 2,012 total
includes taxes & fees
2 Jan - 3 January 2025
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Charming duplex with private yard. Close to the beach, dining & shopping!

9.8 out of 10, Exceptional, (36)
"Duplex unit was clean, as described and perfect for our stay visiting family in Rye. Lots of extra towels and nice welcoming snacks in the kitchen. Super convenient location. Will likely stay there again. "
Charming duplex with private yard. Close to the beach, dining & shopping!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (12)
"Overall, very nice historic home. Very clean, perfect location for our family holiday, wonderful mattresses on all beds, well stocked kitchen with all cooking necessities. Good communication with owners who promptly helped to rectify a few issues. Would recommend to anyone looking to stay in this area."
Historic Hideaway with Lake Access!

TheVictorianBlue|25min to NYC

9.4 out of 10, Exceptional, (3)
"Enough room and bathrooms for all Hostess was gracious and generous God be with you"
TheVictorianBlue|25min to NYC

Modern Colonial House

9.8 out of 10, Exceptional, (17)
"The house was great, the location was great and Carmel was great!"
Modern Colonial House

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (24)
"Pre-stay communication was excellent, with our host contacting me with suggestions for outings (I asked). Our host met us, gave us a tour of the property - not just the living space but the grounds, too. The house is cozy, well thought out and has small touches like a deck of cards (in case you have a couple of minutes of downtime), a beautiful tea set with a variety of delicious teas to use. The house is thoughtfully decorated, the couch and bed are comfortable and there is plenty of space for...
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Pleasantville
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Pleasantville

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is AED 515
AED 592 total
includes taxes & fees
2 Jan - 3 January 2025
Stamford Suites

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (27)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 915 total
includes taxes & fees
29 Dec - 30 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.