Sleepy Hollow Trips (flight + hotel)

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Top hotels in Sleepy Hollow

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 P6,753 per night from Aug 16 to Aug 17
P6,753
P7,765 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very Good! (1,204 reviews)
"Rooms were clean however the bathroom was a little tight for a small family of 3. You can tell they renovated recently which is a plus. Would stay here again if needed to."

Reviewed on Aug 11, 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 P5,537 per night from Aug 24 to Aug 25
P5,537
P6,145 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Room was clean & spacious. Front desk & restaurant did not speak fluent English, & struggled a bit to understand what we were asking, but they were friendly & had a good attitude. The inner courtyard had the potential to be a really nice space, but was in need of some cleaning & landscaping."

Reviewed on Aug 12, 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 P5,258 per night from Aug 24 to Aug 25
P5,258
P5,888 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"Hotel was well cleaned for its age, but was definitely aging. Some of the front desk staff was less than pleasant, but not everyone."

Reviewed on Aug 6, 2025

DoubleTree by Hilton Chicago - Arlington Heights
See all 482 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 vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation 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 vacation 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 vacation package as early as possible.
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 stays and flights individually. Better still, you can personalize 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 vacation package to Sleepy Hollow?
If you have your Sleepy Hollow vacation 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 vacation. 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 personalized Sleepy Hollow vacation package.

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