Pleasantville Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.938.926 ₫ per night from 2 Aug to 3 Aug
3.938.926 ₫
5.163.504 ₫ total
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very good! (1,206 reviews)
"Great stay, beautiful property. Look forward to coming again!"

Reviewed on 28 Jul 2026

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 2.572.858 ₫ per night from 16 Aug to 17 Aug
2.572.858 ₫
3.760.840 ₫ total
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 3.514.406 ₫ per night from 12 Aug to 13 Aug
3.514.406 ₫
4.019.601 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8.4/10 Very good! (1,780 reviews)
"Overall it was a pleasant stay. The front desk staff was warm and accommodating. The room could use a deep cleaning, in particular ; the bathroom, window curtains, the comforter on the bed and the cushions on the sofa."

Reviewed on 29 Jul 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,453 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.
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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.