Pleasantville Holidays from £994

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was £1,759, price is now £994 per person
£994
per person
22 Sept - 29 Sept
found 10 hours ago
Return flight included
Edinburgh (EDI) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Cute hotel

Reviewed on 16 Jul 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,620, price is now £1,847 per person
£1,847
per person
2 Oct - 7 Oct
found 4 hours ago
Return flight included
London (LON) to New York (JFK)
9.2/10 Wonderful! (685 reviews)
Great location, great view

Reviewed on 5 Jul 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £3,882, price is now £2,182 per person
£2,182
per person
2 Oct - 7 Oct
found 4 hours ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,006 reviews)

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 £2,101, price is now £1,190 per person
£1,190
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
The morning buffet was not good , the food was subpar ?.. nothing extraordinary, I felt like I was being herded into an area to eat in a manufacturing factory ..

Reviewed on 16 Jul 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,047, price is now £1,164 per person
£1,164
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)

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

Crowne Plaza Englewood by IHG

Crowne Plaza Englewood by IHG

3.5 out of 5
401 S Van Brunt St Englewood NJ
Fully refundable
The price is £96 per night from 12 Aug to 13 Aug
£96
12 Aug - 13 Aug
includes taxes & fees
8.2/10 Very good! (1,419 reviews)
"When we arrived, we were a little taken aback. The building looked a lot more dated than the pictures. When we got into our room, the bathroom wasn't very clean, so we had to clean it. There was mold along some areas of the shower and around the bathroom. The pictures look much better online than ..."

Reviewed on 16 Jul 2026

Crowne Plaza Englewood by IHG
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is £75 per night from 19 Jul to 20 Jul
£75
19 Jul - 20 Jul
includes taxes & fees
6.2/10 (2,286 reviews)
"1"

Reviewed on 16 Jul 2026

Armoni Inn & Suites
Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

3 out of 5
2167 Route 4 East Fort Lee NJ
Fully refundableReserve now, pay when you stay
The price is £116 per night from 16 Aug to 17 Aug
£116
16 Aug - 17 Aug
includes taxes & fees
Hyatt Place Fort Lee / George Washington Bridge
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly 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

£981
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Pleasantville

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.

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. Flight-inclusive packages are ATOL protected.