Sleepy Hollow Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Sleepy Hollow

Radio Hotel

Radio Hotel

2420 Amsterdam Ave New York NY
4.023.454 ₫
5.420.243 ₫ total
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (2,494 reviews)
"Restaurant was close most of the time only bar open"

Reviewed on 25 Aug 2026

Radio Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
4.866.132 ₫
6.433.432 ₫ total
6 Sept - 7 Sept
includes taxes & fees
Sonesta White Plains Downtown
DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

2117 Route 4 Eastbound Fort Lee NJ
Fully refundableReserve now, pay when you stay
3.217.926 ₫
3.688.548 ₫ total
2 Sept - 3 Sept
includes taxes & fees
DoubleTree by Hilton Fort Lee - George Washington Bridge
See all 1,833 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.
See properties
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.
See properties
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.
See properties

Frequently asked questions

How much does a Sleepy Hollow holiday 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 holiday to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
If you're looking to book a cheap Sleepy Hollow holiday 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 travellers.
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 holiday for longer.
Is it worth booking a holiday 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 holiday.
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 customise 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 holiday as a package?
An Expedia holiday 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 holiday 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 accommodation: After you've settled on your dates and duration, book the perfect Sleepy Hollow holiday package for you.

Explore a world of travel with Expedia