Pleasantville Vacations from ￥278,821

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The Latest Pleasantville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 18 - Sep 22
found 24 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,262 reviews)
Went to see a show at the theater next door,so convenient! And close to Central Park. Will come stay again!😊💖

Reviewed on Aug 12, 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,582 reviews)
The Palace is a classic hotel. The service was outstanding, and the room spacious and clean. We loved our stay!

Reviewed on Aug 12, 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.4/10 Very Good! (1,559 reviews)
Loved this hotel so much. Beds were super comfy & 24 room service is killer

Reviewed on Aug 13, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Loved this affordable Euro-style hotel! The rooms have plenty of space, the neighborhood is amazing, and the rooftop deck is spectacular. Will return for sure!

Reviewed on Aug 12, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to New York (JFK)
9.6/10 Exceptional! (126 reviews)
The hotel was phenomenal! We were greeting so warmly on arrival and given great dining and neighborhood tips by Ben- who was wonderful. The rooms were beautiful and all aspects of the hotel and dining/ bar spaces were gorgeous and full of character. We enjoyed The Portrait Bar a couple of times and had such fun. We also had breakfast in the restaurant and a spectacular dinner at Cafe Carmellini. I wish I could remember our server’s name because she was top notch. I will go back to The Fifth Avenue Hotel. It was a wonderful experience.

Reviewed on Jul 28, 2025

Find the Best Pleasantville Vacation Packages

Pleasantville Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is ￥18,718 per night from Sep 1 to Sep 2
￥18,718
￥21,406 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,104 reviews)
"Older fixtures but clean. Sidewalks in parking area in need of repair."

Reviewed on Aug 9, 2025

Hampton Inn White Plains/Tarrytown
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is ￥21,230 per night from Aug 24 to Aug 25
￥21,230
￥24,281 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,395 reviews)
"N/A"

Reviewed on Aug 9, 2025

Baymont by Wyndham White Plains - Elmsford
Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
7.6/10 Good! (349 reviews)
"It was perfect and affordable!"

Reviewed on Aug 9, 2025

Get rates
Executive Inn - Fort Lee
See all 1,315 properties in Pleasantville
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.

Discover the most popular places to visit in Pleasantville

Jacob Burns Film Center Media Arts Lab

Enjoy the collegiate vibe at Jacob Burns Film Center Media Arts Lab during your stay in Pleasantville. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Jacob Burns Film Center Media Arts Lab

What to do in Pleasantville

Spa-Quality On Demand Massage - Westchester County

Spa-Quality On Demand Massage - Westchester County

￥27,175
per adult
Spa-Quality On Demand Massage - Westchester County
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

￥98,952
per traveler
Introductory Helicopter Flight Lesson from Westchester
See all activities in Pleasantville

Frequently asked questions

How much does a Pleasantville vacation package cost?
You'll find cheap prices from ￥278,821 on Expedia for your Pleasantville getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Pleasantville costs.
What are the cheapest months to go to Pleasantville?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Pleasantville vacation packages and you could score some great off-season deals.
How many days is enough for Pleasantville?
The ideal duration of your Pleasantville vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the major attractions and explore some hidden treasures along the way.
Is it worth booking a vacation package to Pleasantville?
It's easy to see why a Pleasantville vacation is on the to-do list of many travelers. Leading attractions like Rockefeller State Park Preserve are just the start of things to keep you busy here.
How to find the best Pleasantville package deals?
Start your search for a Pleasantville package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Pleasantville package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasantville escape underway.
Is it cheaper to book a Pleasantville vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels individually. Better still, you can personalize your Pleasantville getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Pleasantville?
If you're considering a spontaneous Pleasantville trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Pleasantville?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Pleasantville.
  2. Budget wisely: On top of the price of your hotel, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Pleasantville.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Pleasantville. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Pleasantville vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.