Pleasantville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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.

Top Pleasantville Vacation Deals

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
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (492 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul. 22, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
Nice views.. but food at restaurant left a lot to be desired. Also staff presentation was terrible. They need uniforms and a dress code. Booty shorts, wrinkled clothing... its all a part of the experience and everyone looked like they got up out of bed and came to work. Take pride. Its managements fault ..

Reviewed on Jul. 30, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Sep 14 - Sep 17
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,897 reviews)
Great location - courteous staff.

Reviewed on Aug. 1, 2025

The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Manhattan
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (815 reviews)
Well located on upper east side, very friendly and efficient staff, the most comfortable bed I have ever slept in!

Reviewed on Jul. 21, 2025

Ready to book your vacation to Pleasantville?

 

Choose your dates

Pleasantville Hotel Deals

Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 5 to Aug 6
CA $128
CA $147 total
Aug 5 - Aug 6
includes taxes & fees
7.4/10 Good! (333 reviews)
"Nice room. Bed uncomfortable. Could not use WiFi or cell phone in room."

Reviewed on Jul. 31, 2025

Executive Inn - Fort Lee
Ramada by Wyndham Rochelle Park Near Paramus

Ramada by Wyndham Rochelle Park Near Paramus

2 out of 5
375 W Passaic St, Rochelle Park, NJ
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 4 to Aug 5
CA $151
CA $173 total
Aug 4 - Aug 5
includes taxes & fees
7.2/10 Good! (1,157 reviews)
"Needs work place ok"

Reviewed on Jul. 31, 2025

Ramada by Wyndham Rochelle Park Near Paramus
DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

4 out of 5
2117 Route 4 Eastbound, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Aug 13 to Aug 14
CA $175
CA $200 total
Aug 13 - Aug 14
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"It was clean and the staff were friendly. All the nearby conveniences were close by, which was great."

Reviewed on Jul. 30, 2025

DoubleTree by Hilton Fort Lee - George Washington Bridge
See all 1,299 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Pleasantville

Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

CA $1,302
per traveller
Couple's Private NYC Helicopter Tour from Westchester
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $918
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 $743 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.

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