
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.

The Inn At Fox Hollow Hotel
Price was CA $1,206, price is now CA $720 per person
CA $720
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
The hotel itself was nice. There is truly nothing but senior citizens that stay here. We walked in and thought it was a nursing home. I’m not joking there must have been at least 60 70year olds when we walked in. They just take over the entire hotel. Again, the hotel itself is nice, but I think we would stay somewhere else knowing what we know now especially with two teenage boys with us.
Reviewed on Aug. 28, 2025

1 Hotel Brooklyn Bridge
Price was CA $3,172, price is now CA $1,702 per person
CA $1,702
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,005 reviews)
I had sent two messages to the hotel to check that I had booked the right room type to see the full view ranging from the Brooklyn Bridge, city skyline and all the way to the Statue of Liberty. It is my fault for not following up for a response because I ended up having to choose between the room they gave me (bridge view only) or partial skyline and statue. I chose the statue view but was disappointed as I paid the amount I did expecting the full view. My mistake, not the hotel’s but if you send a message requiring a response, you may not get one. My advise - FOLLOW UP!!! Also, if you have a camera that is anything other than an iPhone, they will not let you use it on the property (from the outside at least). There is mention of this on their website (if it would occur to you to check for such things) but it merely states that no professional photography is permitted without a contract with the property (it does not however state that a camera cannot be used at all) so I was again disappointed to find that this extends to using a hand held fairly basic camera. Most people use their phones I realize, but this is something to be aware of if you plan to use an actual camera or God forbid any type of zoom lense to capture the amazing view. The elevator keys are temperamental and on one occasion I was trapped in the elevator until someone else entered but the staff I encountered were all really friendly and overall it is a really nice hotel in a great location.
Reviewed on Sep. 1, 2025

The Plaza - A Fairmont Managed Hotel
Manhattan
Price was CA $7,372, price is now CA $4,534 per person
CA $4,534
per person
Nov 14 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
June checked us in for The Plaza and was excellent. He was friendly and offered us a room upgrade. We ended up moving to a family suite with 2 queen beds, a sitting area and bar area with a sink and microwave. The room was spectacular. Doormen were also super friendly and bellman was helpful too. The service here is exceptional and the rooms and common areas are beautiful. Highly recommend the hotel for a luxury experience.
Reviewed on Aug. 25, 2025

Kimpton Hotel Eventi by IHG
Manhattan
Price was CA $2,466, price is now CA $1,562 per person
CA $1,562
per person
Nov 14 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,010 reviews)
Staff always take great care of me every time I go I feel like I’m at home away from home
Reviewed on Aug. 21, 2025
Pleasantville Hotel Deals

DoubleTree by Hilton Fort Lee - George Washington Bridge
2117 Route 4 Eastbound, Fort Lee, NJ
The price is CA $164 per night from Oct 1 to Oct 2
CA $164
CA $187 total
Oct 1 - Oct 2
includes taxes & fees

Radio Hotel
2420 Amsterdam Ave, New York, NY
The price is CA $198 per night from Sep 28 to Sep 29
CA $198
CA $261 total
Sep 28 - Sep 29
includes taxes & fees

EVEN Hotel Norwalk by IHG
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $246 per night from Sep 29 to Sep 30
CA $246
CA $283 total
Sep 29 - Sep 30
includes taxes & fees
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 $922
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.