Sleepy Hollow Holidays

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Your Sleepy Hollow Holiday

History, cuisine, art and more … There's so much to discover with a Sleepy Hollow holiday package. And with the ability to customise your city getaway, you know it'll be one that's hard to forget. Ready to explore your surroundings? Grand Victoria Casino, Santas Village and NOW Arena are just a few of the top-rated places to visit during a trip to Sleepy Hollow. Whoever you're heading away with and whatever your budget, your ultimate Sleepy Hollow holiday is just a few clicks away with Expedia.

Sleepy Hollow Holiday

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
3,300
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Santas Village, Hemmens Cultural Centre and Main Beach

Our pick of the best Sleepy Hollow Hotel Deals

Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 10 Aug to 11 Aug
AU$212
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,189 reviews)
"Very clean, there’s a mall nearby and bunch of restaurants"

Reviewed on 4 Aug. 2025

Hyatt Regency Schaumburg 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 AU$174 per night from 17 Aug to 18 Aug
AU$174
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Nice Hotel. Reasonable Price. Room was clean. Property could use updating."

Reviewed on 5 Aug. 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 31 Aug to 1 Sept
AU$160
31 Aug - 1 Sept
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"Vending machines were broken. Toilet was loud and screeched"

Reviewed on 4 Aug. 2025

DoubleTree by Hilton Chicago - Arlington Heights
See all 492 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.