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.
1 Hotel Brooklyn Bridge
Price was CA $4,180, price is now CA $2,473 per person
CA $2,473
per person
Jul 30 - Aug 2
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.
Reviewed on Jun 6, 2026
The Towers at Lotte New York Palace
Manhattan
Price was CA $2,936, price is now CA $1,849 per person
CA $1,849
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (680 reviews)
A clean professional hotel. The down side is that it is very expensive and whilst the staff are very professional, they could not be described as warm and friendly. But maybe that could be said for New York service generally.
Thank you ~ Jon
Reviewed on Jun 20, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was CA $2,070, price is now CA $1,391 per person
CA $1,391
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,636 reviews)
Very nice place to stay in the heart of Times Square! Staff was very helpful and friendly
Would recommend
Reviewed on Jun 28, 2026
Pleasantville Hotel Deals
Crowne Plaza Englewood by IHG
401 S Van Brunt St Englewood NJ
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 13 to Jul 14
CA $159
CA $182 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very good! (1,344 reviews)
"Great stay very accommodating staff great location, safe and friendly"
Reviewed on Jun 27, 2026
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Jun 30 to Jul 1
CA $100
CA $111 total
Jun 30 - Jul 1
includes taxes & fees
6/10 (2,262 reviews)
"The hallways smell like pot and mould, I could see butts under the bed and burn marks on the rug. Housekeeping never came to clean the room or pickup garbage while I stayed there. Its an old property with no restaurant or any amenities including fitness or laundry that work. on the plus side its ..."
Reviewed on Jun 27, 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jul 12 to Jul 13
CA $186
CA $213 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (1,721 reviews)
"The property was in a great location for me, we were checked in with ease, and your front desk person was very helpful with our questions. The facility was clean and well maintained as we walked through. The room was updated and clean and overall plenty comfortable for us. We will be back again."
Reviewed on Jun 27, 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.
Stay near popular Pleasantville attractions
What to do in Pleasantville
Introductory Helicopter Flight Lesson from Westchester
CA $976
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.
