Sleepy Hollow Holidays

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Sleepy Hollow Holiday

Our pick of the best Sleepy Hollow Hotel Deals

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 NZ$185 per night from 16 Aug to 17 Aug
NZ$185
16 Aug - 17 Aug
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"There were pubic hair on the ceiling of our bathroom when brought to the attention of the staff they made jokes and said there was nothing they could do."

Reviewed on 21 July 2026

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 NZ$203 per night from 9 Aug to 10 Aug
NZ$203
9 Aug - 10 Aug
includes taxes & fees
8.2/10 Very good! (1,012 reviews)
"N-a"

Reviewed on 21 July 2026

DoubleTree by Hilton Chicago - Arlington Heights
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
The price is NZ$257 per night from 9 Aug to 10 Aug
NZ$257
9 Aug - 10 Aug
includes taxes & fees
Eaglewood Resort and Spa
See all 480 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.

What to do in Sleepy Hollow

Private Indian-Mexican Fusion Cooking Class in a Chicago Home

Private Indian-Mexican Fusion Cooking Class in a Chicago Home

NZ$173
per adult
Private Indian-Mexican Fusion Cooking Class in a Chicago Home
See all activities in Sleepy Hollow

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.

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