Pleasantville Holidays from £650

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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.
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
29 Sept - 5 Oct
found 1 day ago
Return flight included
London (LON) to New York (JFK)
7/10 Good! (2,169 reviews)
Clean, friendly, easy check in

Reviewed on 13 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
25 Sept - 29 Sept
found 1 hour ago
Return direct flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on 12 Jul 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
18 Aug - 25 Aug
found 1 day ago
Return flight included
London (LGW) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent in every way! And what makes it so coal are the staff members who are so helpful & so friendly.

Reviewed on 13 Jul 2025

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 22 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (232 reviews)
Beautiful hotel from the gilded age. Outstanding service. Beautiful and delicious breakfast.

Reviewed on 4 Jul 2025

The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 22 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9.4/10 Exceptional! (812 reviews)
Excellent hotel with amazing staff.

Reviewed on 24 May 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

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is £92 per night from 4 Aug to 5 Aug
£92
4 Aug - 5 Aug
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Everything!"

Reviewed on 12 Jul 2025

EVEN Hotel Norwalk by IHG
Radio Hotel
Radio Hotel
4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is £113 per night from 14 Jul to 15 Jul
£113
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (2,579 reviews)
"Property was perfectly fine. It was rather small but that's what you expect I suppose in Manhattan. It was a weird thing where we had to buy two drinks for $22 to get the hotel room. I would have preferred not to have had the drink. The bed was comfortable everything was adequate. We were close to ..."

Reviewed on 4 Jul 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
7.4/10 Good! (271 reviews)
"It’s great that they have a convenient and affordable early check in policy. Check in and check are quick. A nice spacious parking lot. And one of the more affordable hotels in the area."

Reviewed on 13 Jul 2025

Get rates
Executive Inn - Fort Lee
See all 1,292 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

Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

£699
per traveller
Couple's Private NYC Helicopter Tour from Westchester
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.