
Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands
Save 100% on your flight
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
This property was okay for a quick stay. The hotel is clearly outdated but it’s not the worst I’ve seen. Beds were comfy and running water was hot. Tub did take awhile to drain but once maintenance came, it worked fine. Ceiling in shower needs repairs. Fridge and microwave were clean. Overall it’s not a 5 star hotel but it’s okay. Pool was fine. Breakfast was basic sausage egg and waffles, option of making your own toast. Staff was polite.
Reviewed on Jul. 14, 2025

Sound View Greenport
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..
Reviewed on Jul. 10, 2025


Outsite Chelsea
Manhattan
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (6 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.
Reviewed on Jun. 25, 2025

Hyatt Regency Jersey City on the Hudson
Downtown Jersey City
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,429 reviews)
Great location! Friendly staff and very clean.
Reviewed on Jul. 6, 2025
Pleasantville Hotel Deals

EVEN Hotel Norwalk by IHG
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $148 per night from Aug 4 to Aug 5
CA $148
CA $170 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Everything!"
Reviewed on Jul. 12, 2025

Radio Hotel
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Jul 20 to Jul 21
CA $210
CA $275 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (2,582 reviews)
"Property was perfectly fine. It was rather small but that's what you expect I suppose in Manhattan. It was a weird thing where we had to buy two drinks for $22 to get the hotel room. I would have preferred not to have had the drink. The bed was comfortable everything was adequate. We were close to ..."
Reviewed on Jul. 4, 2025

Executive Inn - Fort Lee
2339 Route 4, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 3 to Aug 4
CA $128
CA $146 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (281 reviews)
"Room was clean, but the hallways were run down and shabby. There was also some odd odor in the hallways as well."
Reviewed on Jul. 13, 2025
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

Couple's Private NYC Helicopter Tour from Westchester
CA $1,300
per traveller

Introductory Helicopter Flight Lesson from Westchester
CA $917
per traveller
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.