Pleasantville Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Pleasantville Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York
Manhattan
S$2,871
per person
20 Oct - 25 Oct
found 15 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
Such a well situated hotel slap bang in the middle of Manhattan, walking distance to most sightseeing/tourist hubs. Room was fantastic, spacious, tea/coffee making machine, fridge which was a bonus, would 100% stay here again. 5*
Reviewed on 11 Sept, 2026
Top hotels in Pleasantville
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
S$350
27 Sept - 28 Sept
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
S$262
21 Sept - 22 Sept
includes taxes & fees
8.2/10 Very good! (1,292 reviews)
"Felt like a true upscale vacation stay. Class"
Reviewed on 11 Sept, 2026
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
S$171
20 Sept - 21 Sept
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
Shared NYC Helicopter Tour from Westchester
S$529
per traveller
100% of travellers recommend
Private NYC Helicopter Tour From Westchester for 2-6 People
S$2,170
per traveller
Frequently asked questions
How much does a Pleasantville holiday package cost?
You'll find cheap prices from S$1,935 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 holiday 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 holiday packages and you could score some great off-season deals.
How many days is enough for Pleasantville?
The ideal duration of your Pleasantville holiday 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 holiday package to Pleasantville?
It's easy to see why a Pleasantville holiday is on the to-do list of many travellers. 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 holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and hotels individually. Better still, you can personalise 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 holiday 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 customised Pleasantville holiday package.
Explore a world of travel with Expedia
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- Ananda Ashram
- Apollo Theater
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- Visit Mount Kisco
- Mount Sinai Hospital
- Museum of the City of New York
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- Visit Nyack
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- Visit Sleepy Hollow
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- Van Cortlandt Park
- West 71st Street Historic District
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- Woodbury Common Premium Outlets
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
