How much does a Pleasantville vacation package cost?

You'll find cheap prices from $437 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?

Pick your travel dates: The things you want to do in Pleasantville and your favorite season will help you decide when to get away. 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. 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. 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. Bundle your accommodations and airfare: After you've nailed down your dates and duration, lock in the perfect Pleasantville vacation package for you. 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.

Pleasantville Vacation Packages 2026 from $437

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.

Hotel St. James

Manhattan

Save 100% on your flight

$437

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.8/10 Excellent! (7,435 reviews)

Location of hotel was great. Just 2 minutes from Times Square. Everyone at the hotel were very helpful & very friendly 👍

Reviewed on Jun 21, 2026

2 bedroom luxury Empire State VIEW

Manhattan

$1,454

per person

Jul 28 - Jul 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

10/10 Exceptional! (1 review)

Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

1 Hotel Brooklyn Bridge

$1,597

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (1,000 reviews)

Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Topping Rose House

$3,844

per person

Sep 2 - Sep 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

9/10 Wonderful! (152 reviews)

Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.

Reviewed on Mar 24, 2026

Placemakr Wall Street

Manhattan

Save 100% on your flight

$488

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

9.2/10 Wonderful! (934 reviews)

Easy and early check in. Staff was welcoming and helpful. Traveled with a family of 4 (two kids), so the unit was more than enough space and the location suited our needs. Gym and laundry room was a plus! Would definitely stay here again.

Reviewed on Jun 19, 2026

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Pleasantville Hotel Deals

Crowne Plaza Englewood by IHG

401 S Van Brunt St Englewood NJ

Fully refundableReserve now, pay when you stay

$112 nightly

$128 total

Jul 13 - Jul 14

Total with taxes and fees

8.2/10 Very Good! (1,318 reviews)

"The property wasn’t clean, the doors didn’t lock properly and I had to change rooms three times. Took over an hour to finally get settled into a room the the doors didn’t lock locked"

Reviewed on Jun 21, 2026

Armoni Inn & Suites

329 Route 303 Orangeburg NY

Fully refundableReserve now, pay when you stay

$71 nightly

$79 total

Jun 22 - Jun 23

Total with taxes and fees

6/10 (2,254 reviews)

"I’ve stayed there for 4 nights and on my third day when I requested for housekeeping service to be done they totally didn’t do it. I don’t know why but when I got back from work after working a 12-hour shift, my room has not been cleaned and made up at all! So disappointed."

Reviewed on Jun 20, 2026

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

Fully refundableReserve now, pay when you stay

$135 nightly

$155 total

Jun 28 - Jun 29

Total with taxes and fees

8.4/10 Very Good! (1,716 reviews)

"The front the desk employee was so kind and sweet when arriving.She even called to make sure we were all good with our room."

Reviewed on Jun 21, 2026

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.

Things to do near Pleasantville

Pleasantville, New York, is perfect for family-friendly vacations and outdoor adventures. Visitors can enjoy easy walks, friendly attractions, and engaging day tours. The town features a vibrant arts center, theater performances, and educational experiences, making it suitable for all ages. Whether you're seeking romantic getaways or fun at nearby amusement parks, Pleasantville offers a delightful mix of activities to create lasting memories.

Shopping

The Westchester Mall, located 7 miles away, offers a vibrant mix of entertainment and shopping options for all ages. If you're up for a drive, Westchester's Ridge Hill, 12 miles away, features a family-friendly atmosphere. Don’t miss Rockland Bakery, just 11 miles away, for delicious treats.

Recreation

Experience the vibrant atmosphere at Tarrytown Music Hall, just 5 miles away, featuring captivating concerts. For a serene escape, head to Hardscrabble Wilderness Area, located 1 mile from Pleasantville, where you can unwind in nature. Enjoy engaging performances at Westchester Broadway Theatre, 4 miles away, perfect for family fun and romance.

Adventure

Experience the thrill at Sportime USA, an exciting arcadeAdventureZone located 5 miles from Pleasantville, perfect for family fun. For speed enthusiasts, Grand Prix New York / Spins Bowl offers karting adventures 7 miles away. For a unique outdoor experience, Palisades Climb Adventure features ziplining and ropes courses, 9 miles away.

Nightlife

Pleasantville's nightlife offers a lively atmosphere with entertainment and romance vibes. Visit Dave & Buster's for a fun pub experience, or head to the Stonewall Inn and 51-53 Christopher Street for vibrant nightlife, both just a short drive away, featuring great drinks and a welcoming ambiance.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Pleasantville

Pleasantville, New York, is an ideal destination for family vacations, outdoor enthusiasts, and city explorers. Visitors can enjoy a variety of attractions, including urban parks, modern colleges, and nature preserves, all catering to those seeking cultural experiences and family-friendly activities. With an array of tourist hotspots and opportunities for beach getaways, Pleasantville promises a delightful blend of adventure and relaxation for every traveler.

Westchester County Center: Experience the vibrant cultural scene at the Westchester County Center, located 7 miles from Pleasantville. This arts center hosts a variety of performances and events, making it a hub for local and visiting artists.
Rockefeller State Park Preserve: Just 2 miles away, this expansive reserve offers a family-friendly atmosphere with beautiful trails, scenic views, and picnic areas. It's perfect for outdoor activities and enjoying nature.
Kykuit: Explore the historic estate of Kykuit, located 4 miles from Pleasantville. This stunning property boasts impressive gardens, art collections, and rich history, providing a unique glimpse into the lives of the Rockefeller family.

Best time to go to Pleasantville

The best time to visit Pleasantville can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pleasantville falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Pleasantville falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	30.0°F (-1.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	31.6°F (-0.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	49.8°F (9.9°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	60.1°F (15.6°C)	Light Rain	Mostly Sunny	Average	Average
June	68.9°F (20.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Average	Average
September	66.9°F (19.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	56.1°F (13.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	44.2°F (6.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	36.3°F (2.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High

Tips to save on your trip to Pleasantville

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Pleasantville during the low season (January to March) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Language

English

Currency

U.S dollars

Closest Airport

LaGuardia Airport (LGA)

Population

7,200

Max Temp Winter

35ºF

Max Temp Summer

80ºF