Pleasantville Holidays from £1,275

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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.
Wyndham Garden Chinatown

Wyndham Garden Chinatown

4 out of 5
Manhattan
Price was £2,680, price is now £1,275 per person
£1,275
per person
19 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8/10 Very Good! (1,007 reviews)
The room had very comfortable beds and a great view. The staff were incredibly helpful and friendly, especially the concierge who helped with our destinations. We especially enjoyed the breakfast buffet and the convenient location near popular attractions.

Reviewed on 20 Aug 2025

Fairfield Inn & Suites New York Manhattan/Downtown East

Fairfield Inn & Suites New York Manhattan/Downtown East

2.5 out of 5
Manhattan
Price was £2,780, price is now £1,316 per person
£1,316
per person
19 Oct - 23 Oct
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
Estancia cómoda y agradable, el desayuno es bueno, personal amable

Reviewed on 12 Aug 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £2,609, price is now £1,364 per person
£1,364
per person
9 Nov - 13 Nov
just found
Return direct flight included
Edinburgh (EDI) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on 21 Aug 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was £2,992, price is now £1,683 per person
£1,683
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,589 reviews)
Dated rooms at a historic property. Know that before booking and you will enjoy.

Reviewed on 27 Aug 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,455, price is now £1,381 per person
£1,381
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9.8/10 Exceptional! (1,293 reviews)
Great people, great place, rooms are spot on and Rooftop is worth every penny

Reviewed on 26 Aug 2025

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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is £116 per night from 7 Sept to 8 Sept
£116
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,140 reviews)
"The entrance and outside decor needs to be updated."

Reviewed on 25 Aug 2025

Hampton Inn White Plains/Tarrytown
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is £134 per night from 28 Sept to 29 Sept
£134
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (2,640 reviews)
"Very nice"

Reviewed on 19 Aug 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
The price is £79 per night from 2 Sept to 3 Sept
£79
2 Sept - 3 Sept
includes taxes & fees
Executive Inn - Fort Lee
See all 1,300 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

What to do in Pleasantville

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

£493
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.

* 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.