Sleepy Hollow Vacations

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Find the Best Sleepy Hollow Vacation Packages

Sleepy Hollow Hotel Deals

Highbridge Hotel

Highbridge Hotel

1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
₩115,060
₩137,003 total
Aug 27 - Aug 28
includes taxes & fees
Highbridge Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
₩235,593
₩316,465 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
"Amazing breakfast spot clean hotel."

Reviewed on Aug 13, 2026

Sonesta White Plains Downtown
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
₩172,591
₩210,329 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

Royal Regency Hotel
See all 1,849 properties in Sleepy Hollow
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 Sleepy Hollow attractions

A lighthouse with a metal bridge over water during sunset.
Photo by santosh dash

Tarrytown Lighthouse

8.4/10 (104 reviews)
This historic 1883 beacon on the Hudson River showcases a unique caisson design and maritime heritage. Climb its five stories to enjoy panoramic river views and glimpse the fascinating life of lighthouse keepers past.
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A white house with a wooden deck and a wooden bridge over a river.

Philipsburg Manor

8.2/10 (40 reviews)
You can find out about the history of Sleepy Hollow with a trip to Philipsburg Manor. Wander the riverfront in this family-friendly area.
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A historic stone building with a tower and a black iron fence.

Old Dutch Church of Sleepy Hollow

8.6/10 (74 reviews)
This 1685 stone church inspired Washington Irving's "The Legend of Sleepy Hollow" and remains New York's oldest. Wander among historic gravestones where characters from Irving's tale may have found their final rest.
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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You'll find cheap prices on Expedia for your Sleepy Hollow getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
If you're looking to book a cheap Sleepy Hollow vacation package, consider visiting in January, February and March. You're likely to find lower rates on flights and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Sleepy Hollow?
With a well-planned schedule, you can easily hit the main Sleepy Hollow sights in a few days. But if you'd like to discover hidden spots or take day trips, think about booking your Sleepy Hollow vacation for longer.
Is it worth booking a vacation package to Sleepy Hollow?
Sleepy Hollow has everything you need for an awesome trip — nature, culture and history are just the start. Whether you want to check out sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow, or venture off the beaten track, you'll find plenty to see and do on your Sleepy Hollow vacation.
How to find the best Sleepy Hollow package deals?
Landing a cheap Sleepy Hollow package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Sleepy Hollow package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Sleepy Hollow vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Sleepy Hollow getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Sleepy Hollow?
If you've got your Sleepy Hollow travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Sleepy Hollow?
  1. Pick your dates: What you'd like to do in Sleepy Hollow and your preferred season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Sleepy Hollow.
  3. Decide how long to go away for: Now that you know more about Sleepy Hollow, you can figure out the right length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, book the perfect Sleepy Hollow vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.