Sleepy Hollow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Sleepy Hollow Vacation
Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. Grand Victoria Casino, Santas Village and NOW Arena are among the top attractions worth exploring. Whatever your travel plans or budget, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia.
Top Sleepy Hollow Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,322
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago.
We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight.
Other than that, we are very happy.
Reviewed on Aug 18, 2026
Ready to book your vacation to Sleepy Hollow?
Sleepy Hollow Hotel Deals
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
CA $159
CA $207 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,281 reviews)
"I came here to relax, play golf and listen to the great bands for my 52nd bday. My cousin and I had a great time. We are planning to return for a relaxing staycation."
Reviewed on Aug 18, 2026
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
Fully refundableReserve now, pay when you stay
CA $117
CA $134 total
Aug 19 - Aug 20
includes taxes & fees
6.8/10 (1,006 reviews)
"I was disappointed with my room"
Reviewed on Aug 15, 2026
The Westin Chicago Northwest
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
CA $211
CA $236 total
Sep 7 - Sep 8
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'll find cheap prices from CA $1,117 on Expedia for your Sleepy Hollow escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Sleepy Hollow vacation packages and you could score some great off-season discounts.
How many days is enough for Sleepy Hollow?
Generally, a handful of days is enough to tick off the main sights during your Sleepy Hollow vacation. However, if you want to have time to chill out or go on day tours, consider extending your trip.
How to find the best Sleepy Hollow package deals?
Use Expedia's filters to find some great Sleepy Hollow package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break 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 well in advance.
Is it cheaper to book a Sleepy Hollow vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize your Sleepy Hollow trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sleepy Hollow?
If you've got your Sleepy Hollow vacation dates locked in, book early to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Sleepy Hollow?
- Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season will help you decide when to go.
- Set your budget: Consider costs such as food, flights and transportation when calculating how much to put aside for your trip to Sleepy Hollow. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious retreat.
- Decide how many days away: Start by compiling a list of the activities and sights you want to get to in Sleepy Hollow. Then, estimate how long you'll need for each, including any travel time.
- Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, book the perfect Sleepy Hollow vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
