Pleasantville Holidays from AU$1,150

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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.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (1,487 reviews)
The lobby area was welcoming and decorated nicely. Our room was spacious and had a great private balcony. We enjoyed the breakfast pastry and coffee. The only negative was the amount of time it took to check in when we arrived at a non peak time. We also had a visit from housekeeping an hour before checkout which made us feel rushed to leave. I would recommend this location.

Reviewed on 16 Jul. 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
7.8/10 Good! (1,475 reviews)
Amazing landscaping and great views. Property was in a great location along with great customer service and staff

Reviewed on 17 Jul. 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (1,226 reviews)
Excellent location to attend concert at the Beacon and to explore the Upper Westside.

Reviewed on 18 Jul. 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
7.8/10 Good! (2,087 reviews)
I had a fantastic experience here. The rooms are spacious and modern, and the location is perfect for exploring Manhattan. I asked for more toiletries, and they provided everything I needed promptly. Amazing service!

Reviewed on 14 Jul. 2025

Aliz Hotel Times Square

Aliz Hotel Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
8.4/10 Very Good! (1,697 reviews)
Nice for a day trip to broadway

Reviewed on 18 Jul. 2025

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

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is AU$237 per night from 10 Aug to 11 Aug
AU$237
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Overall it was very good. But my only complaint are the carpets. The hall only gets vacuumed every few days. It needs to be cleaned every day. I was seeing the same debris for days. Also, because you allow pets it smells both in hallway and in the rooms. It has this old lingering smell. You need ..."

Reviewed on 16 Jul. 2025

EVEN Hotel Norwalk by IHG
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$249 per night from 31 July to 1 Aug
AU$249
31 July - 1 Aug
includes taxes & fees
8.6/10 Excellent! (2,588 reviews)
"We stayed at this hotel as part of a package with flight and accommodation. The hotel is clean, cozy, and nicely designed. The reception staff were very friendly and welcoming, which made a great impression. Upon check-in, we received drink vouchers — a lovely bonus. We arrived at 3 AM due to a flight ..."

Reviewed on 16 Jul. 2025

Radio Hotel
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
7.4/10 Good! (296 reviews)
"Room was clean, but the hallways were run down and shabby. There was also some odd odor in the hallways as well."

Reviewed on 13 Jul. 2025

Get rates
Executive Inn - Fort Lee
See all 1,292 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

What to do in Pleasantville

Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

AU$1,453
per traveller
Couple's Private NYC Helicopter Tour from Westchester
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

AU$1,025
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$1,150 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.