Pleasantville Vacations from $625

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Your Pleasantville Vacation

Planning your next big adventure is a cinch with a Pleasantville vacation package. The neighborhood of Montrose, which is great for walking, makes a good starting point to uncover the treasures of this lively city. Make your trip to Pleasantville even more enjoyable by including some sightseeing. Van Cortlandt Manor, Tarrytown Music Hall and Sleepy Hollow Cemetery are some of the top attractions worth exploring. Your perfect Pleasantville vacation is just a few clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Pleasantville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 30 - Sep 2
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to New York (JFK)
8.8/10 Excellent! (2,517 reviews)
Front desk team were great. Always enjoy this hotel in this location.

Reviewed on Jun 21, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 7 - Aug 10
just found
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
9.2/10 Wonderful! (549 reviews)
Smart hotel superbly located

Reviewed on Jun 12, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Jul 27 - Jul 31
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to New York (JFK)
8.6/10 Excellent! (1,007 reviews)
I mean it’s the 1hotel

Reviewed on Jun 20, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul 30 - Aug 3
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Nice hotel but rooms are a bit run down. Check in took a very long time and well as getting breakfast but bell staff is super nice and friendly and rooms are very big and spacious

Reviewed on Jun 21, 2024

Candlewood Suites New York City-Times Square, an IHG Hotel

Candlewood Suites New York City-Times Square, an IHG Hotel

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 31 - Sep 7
just found
Roundtrip flight included
San Juan (SJU) to New York (JFK)
8/10 Very Good! (1,015 reviews)
Nice cozy rooms with all amenities. Suitable for long stays. Staff is very cooperative

Reviewed on Jun 18, 2024

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

Pleasantville Hotel Deals

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 Jul 2 to Jul 3
$75
$84 total
includes taxes & fees
Jul 2 - Jul 3
6/10 (1,260 reviews)
"I arrived late at night, and everyone was so sweet. When I got to the room, I didn’t bother checking the lights as I just went to the bathroom and to bed. In the morning the bathroom light did not work. And I was staying two nights, and they accommodated me and got me a whole new room. Thank ..."

Reviewed on Jun 19, 2024

Armoni Inn & Suites
Radio Hotel
Radio Hotel
4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is $122 per night from Jul 21 to Jul 22
$122
$143 total
includes taxes & fees
Jul 21 - Jul 22
8.6/10 Excellent! (1,713 reviews)
"Such a great property. Colorful and a great location. The booking and check in process was so easy. The room was small but a perfect NYC room. Everything we needed. Thank you"

Reviewed on Jun 20, 2024

Radio Hotel
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
The price is $125 per night from Jul 3 to Jul 4
$125
$143 total
includes taxes & fees
Jul 3 - Jul 4
8.2/10 Very Good! (1,043 reviews)
"Everything was Good."

Reviewed on Jun 20, 2024

Baymont by Wyndham White Plains - Elmsford
See all 1,096 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Pleasantville vacation package cost?
We make it easy to see the world, with Pleasantville vacation packages starting from as little as $625. You’ll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few experiences and tours to your itinerary?
How do I get a cheap travel package to Pleasantville?
Our Pleasantville vacation packages promise plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and tours into a handy package. But low prices are just the beginning of your next epic adventure. Book with Expedia and and you’ll have over 550 air carriers and 1,000,000 hotel options throughout the world to choose from. No matter your style or budget, there’s a package with your name on it.
Where should I stay in Pleasantville?
A trip to Pleasantville isn’t complete without visiting Rockefeller State Park Preserve, Jacob Burns Film Center Theater and Westchester Health. Stay close to these tourist attractions and make sightseeing a breeze.
How far in advance should I book my Pleasantville vacation?
It can be difficult to know exactly when is the ideal time to book your vacation to Pleasantville. But typically the earlier you book, the lower the prices. Sometimes, you can book your flights and hotels up to a year prior to departure. If you’re eager to escape on a last-minute getaway, no need to panic! There are fabulous bargains advertised on Expedia every single day.
What does an Expedia Pleasantville travel package include?
Expedia has everything you need to plan your Pleasantville getaway, but what your package looks like is up to you. Select from any combination of rental cars, hotels and flights. After some tours or experiences to keep you on the go? Once you’ve made your booking, you can add them too. No matter your style or budget, there’s a package deal to meet your needs.
What should I know before booking a Pleasantville travel package?
Bundling your bookings into a Pleasantville vacation package is the most convenient way to organize your trip. Not only that, you’ll save big just for combining your hotels, flights and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Pleasantville Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Pleasantville vacation package?
We get it — sometimes life doesn’t go according to plan. If you’ve locked in a Pleasantville vacation package and need to amend or cancel it, we’re here to help. We suggest having a look at our Customer Service Portal first for information. But generally, if you’ve booked your package within 24 hours, you may be able to cancel or change your itinerary for free. If it’s been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Pleasantville

Image for Jacob Burns Film Center Theater

Jacob Burns Film Center Theater

You can enjoy a show at Jacob Burns Film Center Theater during your stay in Pleasantville. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Jacob Burns Film Center Theater
Image for Jacob Burns Film Center Media Arts Lab

Jacob Burns Film Center Media Arts Lab

Enjoy the collegiate vibe at Jacob Burns Film Center Media Arts Lab during your stay in Pleasantville. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Jacob Burns Film Center Media Arts Lab

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.