Pleasantville Holidays from AU$3,019

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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.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$4,932, price is now AU$3,019 per person
AU$3,019
per person
20 Oct - 27 Oct
found 1 day ago
Return direct flight included
Melbourne (AVV) to New York (JFK)
9.8/10 Exceptional! (1,629 reviews)
We loved the NobleDEN! Best location, walkable to everywhere, room had nice view over Grand Street. Would definitely stay again.

Reviewed on 2 Aug 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,508, price is now AU$3,299 per person
AU$3,299
per person
20 Oct - 27 Oct
found 1 day ago
Return direct flight included
Melbourne (AVV) to New York (JFK)
9/10 Wonderful! (3,213 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,315, price is now AU$3,211 per person
AU$3,211
per person
20 Oct - 27 Oct
found 1 day ago
Return direct flight included
Melbourne (AVV) to New York (JFK)
9.2/10 Wonderful! (3,822 reviews)
Great hotel! Felt extremely safe & secure traveling with my daughter. Staff was very helpful & friendly. Busy location right in the theater district. Room was quiet & clean. Would definitely stay again.

Reviewed on 3 Aug 2026

The Evelyn Hotel

The Evelyn Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,527, price is now AU$3,704 per person
AU$3,704
per person
20 Oct - 27 Oct
found 3 hours ago
Return flight included
Melbourne (MEL) to New York (JFK)
9.4/10 Exceptional! (1,329 reviews)
Excellent spot, the best hotel I’ve stayed at in nyc! Comfortable bed, friendly staff, free breakfast, what more could you ask for!

Reviewed on 2 Aug 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$4,956, price is now AU$3,376 per person
AU$3,376
per person
20 Oct - 27 Oct
found 3 hours ago
Return flight included
Melbourne (MEL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)

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

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$203 per night from 17 Aug to 18 Aug
AU$203
17 Aug - 18 Aug
includes taxes & fees
Radio Hotel
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 16 Aug to 17 Aug
AU$292
16 Aug - 17 Aug
includes taxes & fees
Tarrytown House Estate
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is AU$365 per night from 17 Aug to 18 Aug
AU$365
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,330 reviews)
"This property is beautiful! Great stay from start to finish."

Reviewed on 2 Aug 2026

Sonesta White Plains Downtown
See all 1,460 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$1,009
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$3,019 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.