A calm lake surrounded by autumn-colored trees reflecting in the water.

Pleasantville Vacations from $456

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
  • Jan 15 - Jan 18

    Parkway House Goshen Family-Friendly Bed & Breakfast + Flight

    Goshen
    3 nights
    3.0 star property
    9.8/10 - Exceptional (46 reviews)
    "What a amazing property the stuff are amazin"
    Reviewed November 1, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - EWR • Nonstop EWR - ATL • Nonstop
    $738
    $456
    per traveler
    found 19 hours ago
    Parkway House Goshen Family-Friendly Bed & Breakfast
  • Dec 20 - Dec 25

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.0/10 - Wonderful (3,449 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop LGA - ATL • Nonstop
    $2,285
    $1,252
    per traveler
    found 2 days ago
    Hotel Riu Plaza New York Times Square
  • Jan 1 - Jan 4

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - EWR • Nonstop EWR - ATL • Nonstop
    $1,510
    $865
    per traveler
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 14 - Jan 17

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    3 nights
    4.0 star property
    9.2/10 - Wonderful (4,132 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop LGA - ATL • Nonstop
    $806
    $478
    per traveler
    found 2 days ago
    Hotel Riu Plaza Manhattan Times Square
  • Jan 10 - Jan 13

    The Langham, New York, Fifth Avenue + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop EWR - ATL • Nonstop
    $2,279
    $1,384
    per traveler
    found 1 day ago
    The Langham, New York, Fifth Avenue

Where to stay near Pleasantville

Pleasantville, NY, offers a charming blend of family-friendly activities and outdoor adventures. Explore the vibrant Pleasantville Center, a convenient place for dining and shopping, while enjoying its historical atmosphere. Nearby regions in New York provide additional romantic and business-friendly experiences, making it perfect for any traveler.

Thornwood

For travelers seeking a memorable trip, Thornwood offers a charming blend of entertainment and outdoor experiences, perfect for families and weekend getaways. Just a short drive from Pleasantville, visitors can explore the historic Lyndhurst Mansion, enjoy performances at the Westchester County Center, or unwind at the scenic Rockefeller State Park Preserve. With easy access to shopping and recreational venues, Thornwood is a smart choice for your stay, providing a comfortable base to enjoy all that the area has to offer.

Hawthorne

Experience the charm of Hawthorne, a top-rated choice for travelers seeking a blend of business and leisure. This vibrant city offers easy access to attractions like the Westchester County Center, known for its arts events, and the historic Lyndhurst Mansion. Families and weekend getaway enthusiasts will appreciate the nearby sports facility stadium and shopping area. Conveniently located about 2 miles by car from Pleasantville, Hawthorne is an excellent base for your New York adventure, ensuring a memorable stay.

Chappaqua

Make your vacation planning effortless by staying in Chappaqua, a haven for family travelers and weekend getaway seekers due to its proximity to delightful attractions. Enjoy the rich history at Van Cortlandt Manor, explore the arts at the Westchester County Center, or take a scenic stroll near the lake and national state park. Located about 2 miles by car from Pleasantville, Chappaqua offers a charming retreat with plenty to discover, making it a smart choice for your stay.

Briarcliff Manor

Ideally situated for travelers seeking a mix of business and leisure, Briarcliff Manor offers easy access to attractions like the historic Van Cortlandt Manor and the Westchester County Center. This charming city is perfect for weekend getaways or family trips, with a vibrant shopping area and modern square to explore. Located about 3 miles by car from Pleasantville, Briarcliff Manor is a smart choice for your next vacation, blending convenience with local charm.

Pocantico Hills

Travelers seeking a blend of nature and culture will find Pocantico Hills an ideal base for their vacation near Pleasantville. This charming village offers access to attractions like the historic Lyndhurst Mansion and the scenic landscapes of nearby state parks, perfect for outdoor enthusiasts and families alike. With vibrant arts at the Westchester County Center and the modern design of the Governor Mario M. Cuomo Bridge, Pocantico Hills provides a rich experience. It’s just about a 4-mile drive from Pleasantville, making it a smart choice for your stay.

Discover the most popular places to visit in Pleasantville

What to do in Pleasantville

Pleasantville Hotel Deals

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 out more about Pleasantville

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.

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.

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.

Frequently Asked Questions

How much does a Pleasantville vacation package cost?

You'll find cheap prices from $456 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.