Pleasantville Vacation Packages
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Your Pleasantville Vacation
When you book a vacation package to Pleasantville, you can relax and enjoy your getaway knowing that all your travel plans are under control. Discover the many charms of this city while staying in a neighborhood like Montrose, which is great for walking. A trip to Pleasantville is a terrific opportunity to go sightseeing. Be sure to look around renowned attractions like Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility. Whoever you're traveling with and whatever your budget, your dream Pleasantville vacation is only clicks away with Expedia.
Top Pleasantville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
Price was CA $6,110, price is now CA $3,435 per person
CA $3,435
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.
Reviewed on Feb 27, 2026
The Towers at Lotte New York Palace
Manhattan
Price was CA $3,614, price is now CA $2,075 per person
CA $2,075
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (659 reviews)
Great location. Great views in the Towers.
Reviewed on Mar 17, 2026
1 Hotel Central Park
Manhattan
Price was CA $4,868, price is now CA $2,884 per person
CA $2,884
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Everything is great about this Hotel.
Reviewed on Apr 9, 2026
WestHouse New York
Manhattan
Price was CA $2,956, price is now CA $1,779 per person
CA $1,779
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,003 reviews)
Great staff, amazing lunch and breakfast
Reviewed on Apr 9, 2026
Pleasantville Hotel Deals
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Apr 26 to Apr 27
CA $181
CA $207 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (1,647 reviews)
Lady at front desk is rude.
Reviewed on Apr 11, 2026
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 12 to Apr 13
CA $151
CA $216 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (2,561 reviews)
The property was very clean and
Reviewed on Apr 8, 2026
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 12 to Apr 13
CA $192
CA $226 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (470 reviews)
Room and hallway smelled musty and like weed. No pillow cases on one of the beds. Very limited to almost no amenities.. the parking lot has a total of like 8 spots. Would not recommend
Reviewed on Apr 11, 2026
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.
What to do in Pleasantville
Introductory Helicopter Flight Lesson from Westchester
CA $1,705
per traveller
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
