Sleepy Hollow Vacations from ￥250,124
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
￥388,970
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Quaint lil spot that we came back to after our South Bend visit. Great value and location. Comfy beds and quiet. Also amazing food finds with in walking distance.
Reviewed on Oct 17, 2026
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Hotel Deals
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
Fully refundable
￥14,791
￥16,562 total
Nov 15 - Nov 16
includes taxes & fees
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
Fully refundable
￥14,165
￥16,287 total
Nov 15 - Nov 16
includes taxes & fees
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Fully refundable
￥15,311
￥17,604 total
Nov 15 - Nov 16
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.
Frequently asked questions
How much does a Sleepy Hollow vacation package cost?
You can grab a vacation package to this top destination from ￥250,124 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?
- 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 vacation. 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 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.
