Sleepy Hollow Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Sleepy Hollow Vacation Packages

Sleepy Hollow Hotel Deals

Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
121 Northwest Point Boulevard Elk Grove Village IL
The price is AEDĀ 426 per night from Jul 19 to Jul 20
AEDĀ 426
AEDĀ 482 total
19 Jul - 20 Jul
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Very clean and nice rooms"

Reviewed on 16 July 2026

Sheraton Suites Chicago Elk Grove
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 AEDĀ 419 per night from Aug 5 to Aug 6
AEDĀ 419
AEDĀ 469 total
5 Aug - 6 Aug
includes taxes & fees
DoubleTree by Hilton Chicago - Arlington Heights
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 423 per night from Aug 9 to Aug 10
AEDĀ 423
AEDĀ 550 total
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,222 reviews)
"Overall the stay was wonderful. Our trip was cut a bit short because my daughter went into labor. The only inconvenience was having to walk to the pool away from hotel. There was no underground or over pass walkway to get there in the cold. However, Eaglewood is an all time favorite!"

Reviewed on 16 July 2026

Eaglewood Resort and Spa
See all 481 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.

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You'll find cheap prices 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 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 traveling 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 favorite 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.