Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Top Pleasantville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Radio Hotel
Manhattan
CA $1,415
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,493 reviews)
I enjoyed my stay a Radio Hotel. The hotel was clean and comfortable and the staff was very friendly and welcoming, i also loved being able to grab a good cup of coffee downstairs. Overall, I give my stay a 4 out of 5 and would definitely consider staying here again.
Reviewed on Aug 14, 2026
Seven Beach Lane
CA $1,322
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
Ready to book your vacation to Pleasantville?
Pleasantville Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $221
CA $288 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very good! (1,242 reviews)
"Fantastic experience, first time an will be back"
Reviewed on Aug 13, 2026
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
CA $166
CA $233 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (2,461 reviews)
"I enjoyed my stay a Radio Hotel. The hotel was clean and comfortable and the staff was very friendly and welcoming, i also loved being able to grab a good cup of coffee downstairs. Overall, I give my stay a 4 out of 5 and would definitely consider staying here again."
Reviewed on Aug 14, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
CA $152
CA $186 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (2,816 reviews)
"3rd Floor usually has a bad sewer smell ..."
Reviewed on Aug 13, 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.
Stay near popular Pleasantville attractions
Jacob Burns Film Center Media Arts Lab
Take the family on an outing to Jacob Burns Film Center Media Arts Lab during your trip to Pleasantville. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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.
What to do in Pleasantville
Introductory Helicopter Flight Lesson from Westchester
CA $994
per traveller
Frequently asked questions
How much does a Pleasantville vacation package cost?
Offering great value package deals from CA $1,290 on Expedia, you'll be pleasantly surprised at how much a vacation to Pleasantville costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pleasantville?
If you'd like to snag a cheap Pleasantville vacation package, consider travelling in January, February and March. You'll generally find lower rates on hotels and airfares during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Pleasantville?
The ideal duration of your Pleasantville vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Pleasantville?
It's no wonder a Pleasantville vacation is on the to-do list of many travellers. Well-known attractions like Rockefeller State Park Preserve are just the start of things to keep you busy here.
How to find the best Pleasantville package deals?
Use Expedia's filters to help you find some terrific Pleasantville package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Pleasantville package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Pleasantville vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Pleasantville vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Pleasantville?
If you're considering an impromptu Pleasantville getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Pleasantville?
- Pick your travel dates: What you plan to do in Pleasantville and your favourite season can help you decide when to get away.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will likely be the biggest expense during your trip to Pleasantville.
- Decide how long to go for: Now that you're up to speed on Pleasantville, you can work out the right length of your vacation. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Pleasantville vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
