Pleasantville Holidays

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Top hotels in Pleasantville

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 S$253 per night from 2 Aug to 3 Aug
S$253
2 Aug - 3 Aug
includes taxes & fees
Tarrytown House Estate
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is S$191 per night from 16 Aug to 17 Aug
S$191
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (2,506 reviews)
"The staff were very welcoming, and the check in process was very easy. All accommodations included as promised. The restaurant and bar on site was good as well!"

Reviewed on 27 Jul, 2026

Radio Hotel
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is S$200 per night from 27 Aug to 28 Aug
S$200
27 Aug - 28 Aug
includes taxes & fees
8.4/10 Very good! (1,777 reviews)
"Very nice mattress, close to shoping and food. Will stay again."

Reviewed on 28 Jul, 2026

Baymont by Wyndham White Plains - Elmsford
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.

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

S$1,679
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 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.