Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hotel St. James
Manhattan
Price was CA $1,460, price is now CA $896 per person
CA $896
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,381 reviews)
This place was so close to Times Square so walking was a breeze to any good food or subway
Reviewed on May 27, 2026
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $5,745, price is now CA $2,879 per person
CA $2,879
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
New York Marriott Marquis
Manhattan
Price was CA $1,593, price is now CA $963 per person
CA $963
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (4,409 reviews)
Clean room, location staff, breakfast buffet everything great
Reviewed on May 27, 2026
Pleasantville Hotel Deals
Executive Inn - Fort Lee
2339 Route 4 Fort Lee NJ
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from May 28 to May 29
CA $166
CA $190 total
May 28 - May 29
includes taxes & fees
8/10 Very Good! (1,025 reviews)
"The place was runner down. Dirty sheets no blanket. Towels seldom hardly anybody soap. Very disappointed. The continental breakfast no juice/ muffin small seldom and just coffee. The best cleaning people never cleaned my room. Lack of cleanse and no extra toilet paper / towels"
Reviewed on May 26, 2026
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from May 31 to Jun 1
CA $98
CA $109 total
May 31 - Jun 1
includes taxes & fees
6/10 (2,212 reviews)
"大変クリーンでよかったですが、朝食が付いているかと思っていたので、それが残念でした。金額からすれば、良い場所だと思います！！"
Reviewed on May 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 $178 per night from Jun 10 to Jun 11
CA $178
CA $204 total
Jun 10 - Jun 11
includes taxes & fees
8.4/10 Very Good! (1,705 reviews)
"My stay was pleasant the breakfast was a bonus very clean and well stocked. The room was very nice and clean . The pool was a plus also thank you"
Reviewed on May 26, 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 $964
per traveller
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
