
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.

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 The hotel is clearly outdated but it’s not the worst I’ve seen.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

The Harbor Front Inn
Save 100% on your flight
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!
Reviewed on Jul. 11, 2025


Hotel 32 32
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (2,087 reviews)
I had a fantastic experience here. The rooms are spacious and modern, and the location is perfect for exploring Manhattan. I asked for more toiletries, and they provided everything I needed promptly. Amazing service!
Reviewed on Jul. 14, 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
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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.