Sleepy Hollow Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Sleepy Hollow

Grand Royal Hotel O'Hare - Chicago
Grand Royal Hotel O'Hare - Chicago
3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is S$137 per night from 20 Jul to 21 Jul
S$137
20 Jul - 21 Jul
includes taxes & fees
5.6/10 (107 reviews)
"Cheap and convenient to airports"

Reviewed on 9 Jul, 2025

Grand Royal Hotel O'Hare - Chicago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
4 out of 5
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is S$144 per night from 20 Jul to 21 Jul
S$144
20 Jul - 21 Jul
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"The property was clean, staff friendly and a chocolate cookie, warm upon arrival. I was there for 1 night spent most of my time downtown ...There wasn't anything near by, not even a waffle house. You definitely need transportation, your own vehicle preferably."

Reviewed on 10 Jul, 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Comfort Inn Chicago Schaumburg - O'Hare Airport
Comfort Inn Chicago Schaumburg - O'Hare Airport
2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is S$132 per night from 28 Jul to 29 Jul
S$132
28 Jul - 29 Jul
includes taxes & fees
7/10 Good! (860 reviews)
"Cleaning Staff is so kind and polite."

Reviewed on 1 Jul, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
See all 486 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.

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Sleepy Hollow costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Sleepy Hollow?
January, February and November are the best times to search for cheap Sleepy Hollow holiday packages. Choosing to travel in less busy months means you can typically find reduced prices on flights and hotels.
How many days is enough for Sleepy Hollow?
The ideal duration of your Sleepy Hollow holiday depends on what you'd like to do and see. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden gems along the way.
How to find the best Sleepy Hollow package deals?
Use Expedia's filters to find some great Sleepy Hollow package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Sleepy Hollow package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
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 stays and flights individually. Better still, you can personalise your Sleepy Hollow escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Sleepy Hollow?
If you have your Sleepy Hollow holiday dates finalized, book as soon as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Sleepy Hollow?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Sleepy Hollow.
  2. Set your budget: Consider expenses such as transportation, flights and meals when working out how much to put aside for your trip to Sleepy Hollow. Then, select a hotel that matches your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you're more familiar with Sleepy Hollow, you can work out the ideal length of your holiday. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalised Sleepy Hollow holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.