Sleepy Hollow Vacations from $416

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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.

The Latest Sleepy Hollow vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.4/10 Good! (1,003 reviews)
Walking distance Close to woodfield mall, free parking, room are clean. Staff are helpful.

Reviewed on Jul 21, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on Jul 30, 2025

Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8.2/10 Very Good! (1,011 reviews)
Affordable quiet breakfast

Reviewed on Jul 29, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,143 reviews)
The ability to park the car and not have to pay ridiculous amounts of money is very appealing! Close to food, nice location.

Reviewed on Jul 29, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,000 reviews)
Great place will stay again

Reviewed on Jul 31, 2025

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Sleepy Hollow Hotel Deals

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
$101 nightly
The price is $112 total per night from Aug 10 to Aug 11
$112 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (1,027 reviews)
"Our stay was great aside from the shower head spraying water so hard it was spraying out onto the floor. We were unable to adjust the shower head."

Reviewed on Jul 28, 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
900 N Wood Dale Rd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Aug 10 to Aug 11
$119 total
Aug 10 - Aug 11
Total includes taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Very nice hotel"

Reviewed on Jul 27, 2025

Courtyard by Marriott Chicago Wood Dale
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $111 total per night from Aug 7 to Aug 8
$111 total
Aug 7 - Aug 8
Total includes taxes and fees
5.8/10 (133 reviews)
"Pics need to be updated need a lot of updates HOTEL close to airport but close to commercial buildings"

Reviewed on Jul 22, 2025

Grand Royal Hotel O'Hare - Chicago
See all 487 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.

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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You can grab a vacation package to this top destination from $416 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?
December, January and February are great times to look for cheap Sleepy Hollow vacation packages. Choosing to travel in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Sleepy Hollow?
The ideal length for your Sleepy Hollow vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to tick off all the major sights and discover some hidden treasures 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 like can all impact your decision on when to travel to Sleepy Hollow.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Sleepy Hollow.
  3. Explore Sleepy Hollow using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Sleepy Hollow. You can also save your favorite locations, collaborate with your group and manage all your plans in one place.
  4. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Sleepy Hollow. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your accommodations and airfare: Once you've settled on your dates and duration, book the perfect Sleepy Hollow vacation package for you.
  6. Book any activities or excursions: Now to the fun part — organizing everything you want to see and do. Explore some of the top things to do in Sleepy Hollow in Sleepy Hollow and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages?
Your Sleepy Hollow break is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.