Pleasantville Vacation Packages

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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.

Top Pleasantville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Manhattan
Price was CA $1,290, price is now CA $859 per person
CA $859
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very good! (1,515 reviews)
The hotel was good overall and budget friendly. However, limited options for breakfast especially for vegetarians.

Reviewed on Jul 10, 2026

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,528, price is now CA $955 per person
CA $955
per person
Sep 11 - Sep 14
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
They don't have enough air-conditioning. The room was HOT and not in a good way.

Reviewed on Jul 12, 2026

Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Manhattan
Price was CA $1,784, price is now CA $1,123 per person
CA $1,123
per person
Aug 19 - Aug 25
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,011 reviews)
Nice hotel

Reviewed on Jul 11, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,291, price is now CA $3,429 per person
CA $3,429
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was CA $1,521, price is now CA $1,016 per person
CA $1,016
per person
Oct 2 - Oct 5
found 13 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
.

Reviewed on Jul 6, 2026

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Pleasantville Hotel Deals

Crowne Plaza Englewood by IHG

Crowne Plaza Englewood by IHG

3.5 out of 5
401 S Van Brunt St Englewood NJ
Fully refundable
The price is CA $161 per night from Aug 3 to Aug 4
CA $161
CA $185 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very good! (1,408 reviews)
"Me quedé por 14 días y ellos con la limpieza no son tan limpios , dejan mucho polvo y no limpian el piso bien tampoco ósea la alfombra"

Reviewed on Jul 11, 2026

Crowne Plaza Englewood by IHG
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 23 to Jul 24
CA $118
CA $131 total
Jul 23 - Jul 24
includes taxes & fees
6/10 (2,292 reviews)
"Smelly rooms- had humidity smell throughout. Not clean towels"

Reviewed on Jul 12, 2026

Armoni Inn & Suites
Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

3 out of 5
2167 Route 4 East Fort Lee NJ
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Aug 9 to Aug 10
CA $203
CA $232 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (2,043 reviews)
"La atencion muy buena"

Reviewed on Jul 11, 2026

Hyatt Place Fort Lee / George Washington Bridge
See all 1,454 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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Stay near popular Pleasantville attractions

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.
See properties

What to do in Pleasantville

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $1,844
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Pleasantville

Frequently asked questions

How much does a Pleasantville vacation package cost?
Offering great value package deals from CA $859 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?

  1. Pick your travel dates: What you plan to do in Pleasantville and your favourite season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.