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.
Level Chicago – Old Town
Downtown Chicago
CA $1,508
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,137
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!
Reviewed on Sep 21, 2026
Ready to book your vacation to Sleepy Hollow?
Sleepy Hollow Hotel Deals
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
CA $175
CA $226 total
Oct 2 - Oct 3
includes taxes & fees
8.8/10 Excellent! (1,353 reviews)
"Clean rooms"
Reviewed on Sep 21, 2026
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Fully refundableReserve now, pay when you stay
CA $202
CA $232 total
Oct 1 - Oct 2
includes taxes & fees
8.6/10 Excellent! (1,472 reviews)
"Complimentary shuttle for guest transportation anywhere within a 4 mile radius is such an awesome perk of staying here! The lobby is phenomenally designed to create a ton of space for all guests to lounge without feeling overcrowded. It’s obvious the hotel has undergone some major renovations, but ..."
Reviewed on Sep 21, 2026
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
CA $170
CA $188 total
Oct 18 - Oct 19
includes taxes & fees
7.8/10 Good! (1,050 reviews)
"We had great experiences here. But last night, there were stains all over our bed, and the room wasn’t even vacuumed…. There was no breakfast buffet. It just wasn’t a good experience.. especially celebrating our anniversary."
Reviewed on Sep 20, 2026
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 $1,030 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.
