Pleasantville Vacations from $290

Book a Hotel + Flight or Car together to unlock savings

Your Pleasantville Vacation

When you book a vacation 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 neighborhood 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 traveling with and whatever your budget, your dream Pleasantville vacation is only clicks away with Expedia.

The Latest Pleasantville vacation packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad
The Inn At Fox Hollow Hotel
The Mansion at Glen Cove
1 Hotel Central Park
Newark Liberty International Airport Marriott
Don't see what you're looking for?
See all available trips from Columbus to Pleasantville
View all trips

Discover the most popular places to visit in Pleasantville

What to do in Pleasantville

Pleasantville Hotel Deals

DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

4 out of 5
2117 Route 4 Eastbound, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $149 total per night from Nov 9 to Nov 10
$149 total
Nov 9 - Nov 10
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
clean and friendly staffs

Reviewed on Oct 27, 2025

DoubleTree by Hilton Fort Lee - George Washington Bridge
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
$132 nightly
The price is $151 total per night from Nov 9 to Nov 10
$151 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,434 reviews)
The room was spotless along with the rest of the facility, very impressed. The front staff was efficient and professional, but far from friendly. Never a smile or a hello, just did their work well. I had a mis-understanding with a room and they accommodated quickly. Breakfast was basic but OK.

Reviewed on Oct 31, 2025

Baymont by Wyndham White Plains - Elmsford
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
$98 nightly
The price is $112 total per night from Dec 1 to Dec 2
$112 total
Dec 1 - Dec 2
Total with taxes and fees
7.6/10 Good! (577 reviews)
The room was clean and comfortable

Reviewed on Oct 29, 2025

Executive Inn - Fort Lee
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.

Find the Best Pleasantville Vacation Packages

Pleasantville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
7,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Capitol Theatre, Legoland Discovery Center Westchester and Franklin D. Roosevelt State Park

More vacations you might like

Frequently asked questions

How much does a Pleasantville vacation package cost?
You'll find cheap prices from $290 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 vacation to Pleasantville costs.
What are the cheapest months to go to Pleasantville?
If you're looking to snag a cheap Pleasantville vacation package, consider traveling in December, January and February. You'll typically find better prices on accommodations and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Pleasantville?
Usually, a handful of days is enough to visit the main attractions during your Pleasantville vacation. But if you prefer to have some time to kick back or take day trips, think about extending your trip.
Is it worth booking a vacation package to Pleasantville?
Pleasantville offers everything you need for an unforgettable getaway. Get your Pleasantville vacation off to a flying start by visiting top attractions like Rockefeller State Park Preserve.
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 vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels individually. Better still, you can personalize 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 vacation 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. Pick your travel dates: The things you want to do in Pleasantville and your favorite season will help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Pleasantville.
  3. Discover Pleasantville using Expedia's trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Pleasantville. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Pleasantville, you can work out the ideal length of your break. Pull together a rough plan and give yourself enough time for all the things you want to do.
  5. Bundle your accommodations and airfare: After you've nailed down your dates and duration, lock in the perfect Pleasantville vacation package for you.
  6. Book any excursions or activities: Now to the fun part — locking in everything you want to do and see. Explore some of the incredible things to do in Pleasantville in Pleasantville and book your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Pleasantville vacation packages?
Jet off on your perfect trip to Pleasantville with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snag great deals before they disappear.

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.