Pleasantville Holidays from NZ$3,252
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The Latest Pleasantville Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
NZ$4,525
per person
30 Nov - 3 Dec
found 1 day ago
Return flight included
Christchurch (CHC) to New York (JFK)
9.2/10 Wonderful! (3,950 reviews)
Wallace at front desk was excellent as well as the rest of the Riu team. Housekeeping was superb!
Reviewed on 17 Sept 2026
Pleasantville Holiday
Our pick of the best Pleasantville Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
NZ$482
27 Sept - 28 Sept
includes taxes & fees
8.4/10 Very good! (2,427 reviews)
"This hotel looks far better online, than it does in-person. Rooms had visible wear and tear, rooms were humid and dusty! Staff was helpful, but the property overall needs improvement! I WOULDN’T RECOMMEND!"
Reviewed on 17 Sept 2026
DoubleTree by Hilton Fort Lee - George Washington Bridge
2117 Route 4 Eastbound Fort Lee NJ
Fully refundableReserve now, pay when you stay
NZ$261
1 Oct - 2 Oct
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
NZ$361
4 Oct - 5 Oct
includes taxes & fees
8.2/10 Very good! (1,302 reviews)
"Beautiful property and grounds! Very friendly staff."
Reviewed on 17 Sept 2026
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 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.
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.
What to do in Pleasantville
Spa-Quality On Demand Massage - Westchester County
NZ$308
per adult
Shared NYC Helicopter Tour from Westchester
NZ$694
per traveller
100% of travellers recommend
Private NYC Helicopter Tour From Westchester for 2-6 People
NZ$2,860
per traveller
Frequently asked questions
How much does a Pleasantville holiday package cost?
You'll find cheap prices from NZ$3,252 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
