Sleepy Hollow Vacation Packages

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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.

Top Sleepy Hollow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,139 reviews)
The view @ location was amazing!!!!

Reviewed on Aug. 3, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Very friendly staff!

Reviewed on Aug. 3, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,922 reviews)
We spent 4 nights and had no major complaints. I don't understand why there was an additional mandatory destination fee for normal amenities that we did not ask for or use.

Reviewed on Aug. 1, 2025

Ready to book your vacation to Sleepy Hollow?

 

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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
The price is CA $139 per night from Aug 10 to Aug 11
CA $139
CA $155 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Food options were perfect for breakfast in the morning. Nice and fresh and constantly stocked! The beds were fairly comfortable with nice and warm sheets!!"

Reviewed on Aug. 2, 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
The price is CA $128 per night from Aug 10 to Aug 11
CA $128
CA $142 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Room condition and staff help was excellent. Not happy with the cost of breakfast."

Reviewed on Aug. 2, 2025

Courtyard by Marriott Chicago Wood Dale
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 10 to Aug 11
CA $128
CA $143 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"The lady at the desk was pleasant."

Reviewed on Aug. 1, 2025

DoubleTree by Hilton Chicago - Arlington Heights
See all 492 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
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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You'll find cheap prices from CA $1,010 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?

  1. Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.