Pleasantville Holidays from NZ$5,268

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The Latest Pleasantville Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was NZ$8,008, price is now NZ$5,268 per person
NZ$5,268
per person
26 Dec - 1 Jan
found 19 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (275 reviews)
Perfect location

Reviewed on 30 Oct 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was NZ$10,635, price is now NZ$6,733 per person
NZ$6,733
per person
21 Dec - 28 Dec
found 18 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was NZ$9,272, price is now NZ$6,306 per person
NZ$6,306
per person
21 Dec - 28 Dec
found 18 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
wonderful stay and well located.....

Reviewed on 28 Oct 2026

Pendry Natirar

Pendry Natirar

5 out of 5
Price was NZ$11,039, price is now NZ$7,624 per person
NZ$7,624
per person
21 Dec - 28 Dec
found 18 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (23 reviews)
The property itself is excellent, and both the restaurant and the food were outstanding. Unfortunately, the rooms did not live up to the same standard, especially considering the price we paid. They felt unfinished, almost as though the budget had run out before the interior decoration was completed. The furniture was also quite worn and showed signs of age and heavy use. Overall, while we really enjoyed the property and dining experience, the rooms were disappointing. At this price point, I expected a much higher level of quality, attention to detail, and overall refinement. Make the review more direct and forcefulAdd a stronger recommendation warning

Reviewed on 25 Oct 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was NZ$18,925, price is now NZ$13,102 per person
NZ$13,102
per person
21 Dec - 28 Dec
found 19 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

Pleasantville Holiday

Our pick of the best Pleasantville Hotel Deals

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
The price is NZ$240 per night from 3 Nov to 4 Nov
NZ$240
3 Nov - 4 Nov
includes taxes & fees
Executive Inn - Fort Lee
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is NZ$364 per night from 22 Nov to 23 Nov
NZ$364
22 Nov - 23 Nov
includes taxes & fees
Radio Hotel
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Get rates
Armoni Inn & Suites
See all 1,445 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.

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.
See properties

What to do in Pleasantville

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

NZ$1,242
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Pleasantville

Frequently asked questions

How much does a Pleasantville holiday package cost?
You'll find cheap prices from NZ$5,268 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?

  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 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.