Pleasantville Vacations from $381

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (548 reviews)
Thank you Adrian. She was wonderful and made my mother’s birthday special. Every interaction we had with the staff was positive. The halyard served a delicious lobster roll in a beautiful setting. We will be back.

Reviewed on Aug 9, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (495 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.

Reviewed on Aug 14, 2025

Harpoon House

Harpoon House

3 out of 5
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (125 reviews)
Pop Up Rocco was excellent—bed was crisp & comfortable

Reviewed on Aug 15, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on Aug 6, 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

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
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,111 reviews)
"Location great for access to Tarrytown train. Clean and friendly."

Reviewed on Aug 14, 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
$146 nightly
The price is $171 total per night from Aug 18 to Aug 19
$171 total
Aug 18 - Aug 19
Total includes taxes and fees
8.6/10 Excellent! (2,628 reviews)
"Very warm clean environment the staff was above and beyond"

Reviewed on Aug 13, 2025

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
$144 nightly
The price is $164 total per night from Aug 24 to Aug 25
$164 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,394 reviews)
"N/A"

Reviewed on Aug 9, 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,315 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.

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Frequently asked questions

How much does a Pleasantville vacation package cost?
You'll find cheap prices from $381 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.