Sleepy Hollow Vacations from $261

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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.
MainStay Suites Northbrook Wheeling

MainStay Suites Northbrook Wheeling

2.5 out of 5
per person
Jul 24 - Jul 27
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (882 reviews)
Great place for one person for leaving, better than apartment👍

Reviewed on Apr 4, 2025

Motel 6 Joliet, IL - I-80

Motel 6 Joliet, IL - I-80

2 out of 5
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (CHI)
5.4/10 (611 reviews)
Thank you for a cheap priced hotel room with wow factor design!

Reviewed on Apr 6, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr 28, 2025

Holiday Inn Express Hotel & Suites, a Lake Zurich-Barrington by IHG

Holiday Inn Express Hotel & Suites, a Lake Zurich-Barrington by IHG

2.5 out of 5
per person
Jun 20 - Jun 22
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.8/10 Excellent! (776 reviews)
Parking in strip mall

Reviewed on Apr 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
It was really nice overall! Would recommend

Reviewed on Apr 28, 2025

Find the Best Sleepy Hollow Vacation Packages

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
3,300
Top Sights
Santas Village, Hemmens Cultural Center and Epic Air Trampoline Park

Ready to book your vacation to Sleepy Hollow?

 

Choose your dates

Sleepy Hollow Hotel Deals

Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is $123 per night from May 4 to May 5
$123
includes taxes & fees
$107 per night
May 4 - May 5
8.4/10 Very Good! (1,048 reviews)
"Loved everything"

Reviewed on Apr 28, 2025

Hyatt Regency Schaumburg Chicago
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Fully refundableReserve now, pay when you stay
The price is $116 per night from May 11 to May 12
$116
includes taxes & fees
$103 per night
May 11 - May 12
8.4/10 Very Good! (1,009 reviews)
"Stay was great"

Reviewed on Apr 27, 2025

Hyatt Place Chicago/Hoffman Estates
Hyatt Place Itasca
Hyatt Place Itasca
3 out of 5
1150 North Arlington Heights Road, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is $105 per night from May 6 to May 7
$105
includes taxes & fees
$95 per night
May 6 - May 7
"Very nice hotel, very clean, like it."

Reviewed on Apr 28, 2025

Hyatt Place Itasca
See all 483 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You can grab a vacation package to this top destination from $261 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.