Pleasantville Vacations from $253

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $553, price is now $253 per person
$253
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.4/10 Good! (5,413 reviews)
Amenities were underwhelming. The breakfast is a typical continental breakfast you could find at any hotel, you just might pay $38 here for it if it’s not included.

Reviewed on Dec 1, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $627, price is now $287 per person
$287
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
We loved it and the restaurant but for Friday night. We were on the 10th floor and the he music from the Event space on the 12th floor shock and pounded us till 4 am. If you like to sleep at night come here weeknights ONLY!

Reviewed on Nov 29, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $786, price is now $374 per person
$374
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
Friendly professional staff! Lovely gift on check in….clean lovely modern room. Very impressed!

Reviewed on Nov 30, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $786, price is now $385 per person
$385
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (3,348 reviews)
Clean, quick check in

Reviewed on Dec 1, 2025

Hotel Hendricks

Hotel Hendricks

4 out of 5
Manhattan
Save 100% on your flight
Price was $595, price is now $301 per person
$301
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (1,728 reviews)
Hotel Hendricks is in the perfect location to explore Manhattan, just a few blocks from Bryant Park

Reviewed on Nov 26, 2025

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Discover the most popular places to visit in Pleasantville

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

Pleasantville Hotel Deals

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
$127 nightly
The price is $145 total per night from Dec 15 to Dec 16
$145 total
Dec 15 - Dec 16
Total with taxes and fees
8.2/10 Very Good! (1,464 reviews)
Staff, amenities, and clean rooms. The staff was super friendly and accommodating. Great experience and stay will come again!

Reviewed on Nov 25, 2025

Baymont by Wyndham White Plains - Elmsford
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $253 total per night from Dec 21 to Dec 22
$253 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,633 reviews)
Price was right. Room had some problems - lamps and believe or not the Radio weren't working. They offered to send someone up, but we declined, preferring to go to sleep that night. Staff was good, bed and TV good. The bathroom could have used at least a little bit of counter space - essentially, ...

Reviewed on Nov 28, 2025

Radio Hotel
Ramada by Wyndham Rochelle Park Near Paramus

Ramada by Wyndham Rochelle Park Near Paramus

2 out of 5
375 W Passaic St Rochelle Park NJ
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Dec 2 to Dec 3
$111 total
Dec 2 - Dec 3
Total with taxes and fees
7.2/10 Good! (1,287 reviews)
Awesome

Reviewed on Nov 27, 2025

Ramada by Wyndham Rochelle Park Near Paramus
See all 1,366 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.

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

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Frequently asked questions

How much does a Pleasantville vacation package cost?
You'll find cheap prices from $253 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.