Sleepy Hollow Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
€1,761
per person
28 Nov - 4 Dec
found 19 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
At check-in there was a high security deposit fee of $100.00 a night. After checkout we received a receipt for an additional charge of $34.95 a nightfor something called Nightly Service Fee. In addition there was a state sales tax of $3.58 and a service tax of $0.35 per night which added up to a total addition of $116.64 to what I pre-paid for. three nights. I am not happy.
Reviewed on 11 Sept 2026
Top hotels in Sleepy Hollow
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
€136
13 Sept - 14 Sept
includes taxes & fees
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
€107
11 Oct - 12 Oct
includes taxes & fees
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Fully refundableReserve now, pay when you stay
€126
11 Oct - 12 Oct
includes taxes & fees
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
€85
per adult
Frequently asked questions
How much does a Sleepy Hollow holiday package cost?
You can grab a holiday package to this top destination from €1,612 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?
- 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.
- 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.
- 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.
- 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.
