Pleasantville Vacations from ￥535,337
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The Latest Pleasantville Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Marco LaGuardia Hotel
Queens
￥545,922
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,246 reviews)
Nice quality hotel with very helpful and friendly staff. Good quality breakfast with good hot food options. Excellent Italian restaurant on site with homemade pasta and homemade gelato and sorbetto. Very good shuttle service to airport and U.S. Open tennis center. Clean room with comfortable beds.
Reviewed on Sep 12, 2026
42 Hotel
￥570,875
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (965 reviews)
Pros:
- clean and nice
Cons:
- sits next too a carwash which starts a loud white noise at 9am. this may bug you or not
- my stated check-in time was delayed an hour, because they didnt have enough staff to clean rooms
Reviewed on Sep 11, 2026
Find the Best Pleasantville Vacation Packages
Pleasantville Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
￥31,748
￥41,146 total
Sep 27 - Sep 28
includes taxes & fees
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
￥18,138
￥20,745 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very Good! (1,649 reviews)
"The hotel was clean, but housekeeping is only every other day of each stay and our room was skipped entirely during our three night stay. The humidity in our room was also way too high, and running the A/C only seemed to make it feel more clammy, almost as if there was a humidifier running."
Reviewed on Sep 12, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
￥19,570
￥23,812 total
Sep 28 - Sep 29
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.
Stay near popular Pleasantville attractions
Jacob Burns Film Center Media Arts Lab
This creative learning hub offers state-of-the-art facilities for filmmaking, animation, and screenwriting. Register early for hands-on media workshops where you'll develop storytelling skills in professional studios.
Jacob Burns Film Center Theater
This renowned five-screen cinema showcases independent, foreign, and documentary films in an intimate setting. Enjoy special events with filmmakers at the Take 3 Wine Bar & Café before your screening.
What to do in Pleasantville
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
￥800
per adult
Spa-Quality On Demand Massage - Westchester County
￥29,457
per adult
Introductory Helicopter Flight Lesson from Westchester
￥112,863
per traveler
Frequently asked questions
How much does a Pleasantville vacation package cost?
You'll find cheap prices from ￥535,337 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?
- 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.
- 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.
- 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.
- 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.
