Pleasantville Holidays from £838
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Your Pleasantville Holiday
When you book a holiday package to Pleasantville, you can relax and enjoy your getaway knowing that all your travel plans are under control. Discover the many charms of this city while staying in a neighbourhood like Montrose, which is great for walking. A trip to Pleasantville is a terrific opportunity to go sightseeing. Be sure to look around renowned attractions like Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility. Whoever you're travelling with and whatever your budget, your dream Pleasantville holiday is only clicks away with Expedia.
Top Pleasantville Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC
Southeast Yonkers
£852
per person
2 Nov - 8 Nov
found 10 hours ago
Return flight included
Manchester (MAN) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on 29 Jun 2026
1 Hotel Central Park
Manhattan
£1,912
per person
22 Oct - 27 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,020 reviews)
The hotel is in a great location but was disappointed in my room. The closet was more like a cupboard and I had to get creative on hanging my
clothes. There is no chest for drawers. The lighting switches are confusing but figured them out. Even on the full lighting, the room is dim. The staff was great.
Reviewed on 30 Aug 2026
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 |
Top hotels in Pleasantville
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
£155
1 Sept - 2 Sept
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
£153
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (1,272 reviews)
"The grounds and outside lawns and gardens are beautiful, but the interior seems somewhat old and run down."
Reviewed on 30 Aug 2026
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
£96
6 Sept - 7 Sept
includes taxes & fees
8/10 Very good! (1,630 reviews)
"The hotel staff is professional and friendly. The property and hotel are clean."
Reviewed on 30 Aug 2026
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 Media Arts Lab
This creative learning hub offers state-of-the-art facilities for filmmaking, animation, and screenwriting. Register early for hands-on media workshops where you'll develop storytelling skills in professional studios.
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.
What to do in Pleasantville
Introductory Helicopter Flight Lesson from Westchester
£517
per traveller
Frequently asked questions
Why should I book my Pleasantville holiday with Expedia?
With exceptional-value flights, car hire and hotel options all in one place, Expedia makes booking your Pleasantville adventure a cinch. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from wonderful stays, add your flights and/or a car hire (and maybe also some fun activities!) and score unbeatable prices. Need to cancel? Expedia offers a flexible cancellation policy for many bookings. To find out more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Pleasantville?
If you enjoy the buzz of peak season, visit Pleasantville in April, July and August. If you'd like a more relaxed vibe, December, January and February are better times to visit. With average daytime temperatures of -1ºC, January is the coolest period in Pleasantville. The warmest time of year is July, when you can experience averages of 24ºC throughout the day. Whatever the temperature, you'll find loads to keep you occupied here.
How do I get a cheap holiday to Pleasantville?
Creating your own Pleasantville holiday with Expedia is an easy way to save. We have access to more than 400 partner airlines and 321,000 hotels spread across the globe. With such a fantastic range to pick from, you'll have no issues putting together your next dream getaway. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Pleasantville holiday?
Offering major attractions such as Westchester Medical Centre and Rockefeller State Park Preserve, a holiday in Pleasantville promises plenty of exciting things to see and do. New York Medical College and Jacob Burns Film Centre Media Arts Lab are two other sights also worth a look.
What is the best area to stay in when on holiday in Pleasantville?
If you plan to visit Rockefeller State Park Preserve, maximise your time sightseeing and book a stay close by. It's one of the top attractions in Pleasantville.
Do I need a visa for my Pleasantville holiday?
Visa requirements for Pleasantville vary depending on your nationality and reason for your visit. Make sure you check official government websites to determine if you need a visa for your holiday. They'll also give you the most up-to-date information, including details about application procedures and any supporting documentation that may be necessary. Enquire about your visa requirements well in advance to ensure a travel experience that's hassle free. Also double-check to see that your passport is valid for a further six months from your planned return date.
What should I wear on my Pleasantville holiday?
Though everyone's personal style differs, it can be helpful to have some guidelines for what type of clothes to bring on your holiday in Pleasantville. Think about browsing social media before you leave for inspiration on local fashion trends.
What does an Expedia Pleasantville holiday include?
Hotels, car hires and flights, or any combination of the three — it's up to you! Whether you're visiting Pleasantville with the entire family or enjoying a solo break, there's a bundle to fit your budget and style. Once you've made your booking, why not add on one or two activities? Expedia features many styles of properties, with the most sought-after in Pleasantville being private holiday homes and cottages. Whatever retreat you're after, Expedia gives you the flexibility and freedom to tailor your holiday to suit your needs.
Does Expedia offer Book Now, Pay Later Pleasantville holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If paying over multiple transactions sounds right for you, pick this option at checkout.
- No-deposit holidays: If not paying upfront for your getaway makes pressing that "book now" button easier, go for a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Pleasantville Expedia holiday?
Yes, you sure can. We offer more than 400 airline partners across the globe, so go with the carrier that best suits your budget and travel needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
