Pleasantville Holidays from AU$992

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Your Pleasantville Holiday

Simplify your travel planning with a Pleasantville holiday package. A great neighbourhood to base yourself in this fascinating city is Montrose, which is good for walking and much more. Fill your schedule with visits to Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall, some of the attractions you simply have to see during a trip to Pleasantville. Whatever your travel plans or the size of your budget, organising your ultimate tailored Pleasantville holiday is simple with Expedia.

The Latest Pleasantville Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Queens
Price was AU$1,405, price is now AU$992 per person
AU$992
per person
14 Dec - 17 Dec
found 5 hours ago
Return direct flight included
Nashville (BNA) to New York (JFK)
7.2/10 Good! (536 reviews)
First things first: if you're staying less than a week, they will add a nightly surcharge to your bill. This was not listed on Expedia. There is rarely anyone at the front desk. Everything is done electronically. It's really hard to check in by phone, and because of location, coming back at night can feel a little scary. The place is not as well kept up as previous owners had kept it. There are stains in the hall rugs. Photo-sensitive hall lights are late coming on. Two lamps in my room did not work. Don't expect maid service during your stay, nor was the room service all that complete. There were dishes in the dishwasher when I checked in. The HVAC unit is inconsistent. It resets the temperature on its own, so if you like to sleep cold, be prepared to wake up in a sweat.

Reviewed on 1 Nov 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was AU$2,299, price is now AU$1,446 per person
AU$1,446
per person
14 Dec - 17 Dec
found 8 hours ago
Return flight included
Nashville (BNA) to New York (JFK)
9.4/10 Exceptional! (275 reviews)

Royalton New York

Royalton New York

4 out of 5
Manhattan
Price was AU$1,564, price is now AU$1,073 per person
AU$1,073
per person
14 Dec - 17 Dec
found 1 day ago
Return flight included
Nashville (BNA) to New York (JFK)
7.8/10 Good! (1,005 reviews)

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was AU$1,451, price is now AU$1,046 per person
AU$1,046
per person
14 Dec - 17 Dec
found 5 hours ago
Return direct flight included
Nashville (BNA) to New York (JFK)
6.8/10 (2,161 reviews)
Perfect location

Reviewed on 2 Nov 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was AU$3,005, price is now AU$2,192 per person
AU$2,192
per person
14 Dec - 17 Dec
found 5 hours ago
Return direct flight included
Nashville (BNA) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
wonderful stay and well located.....

Reviewed on 28 Oct 2026

Pleasantville Holiday

Pleasantville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
7,200
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Jacob Burns Film Centre Theatre, Rockefeller State Park Preserve and New York Medical College

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 AU$192 per night from 3 Nov to 4 Nov
AU$192
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 AU$292 per night from 22 Nov to 23 Nov
AU$292
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

AU$1,015
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 AU$992 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.