Sleepy Hollow Vacations from $564

Book a Hotel + Flight or Car together to unlock savings

Your Sleepy Hollow Vacation

When you book a Sleepy Hollow vacation package, it's all about enjoying your adventure to the fullest. Delve into the best things about this exciting city knowing that everything has been taken care of in advance. If taking in sights is part of the plan during your trip to Sleepy Hollow, check out big attractions like Santas Village, Grand Victoria Casino and NOW Arena. Whoever you're taking a break with and whatever you want to spend, your dream Sleepy Hollow vacation is just a few clicks away with Expedia.

The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 3
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 3
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,486 reviews)
Hated that the gps kept taking me to the back of the hotel which made hard to find

Reviewed on May 3, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 17 - Jul 23
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
8.2/10 Very Good! (1,009 reviews)
Staff very friendly and helpful. Rooms were good. No coffee makers in rooms which is a bit different but each morning complimemtary coffee was available in the lobby. Really good location for us and we would highly reccommend.

Reviewed on May 14, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 3
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 3
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

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

Sleepy Hollow Hotel Deals

Best Western O'Hare/Elk Grove Hotel
Best Western O'Hare/Elk Grove Hotel
3 out of 5
100 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is $87 per night from Jun 3 to Jun 4
$87
$98 total
includes taxes & fees
Jun 3 - Jun 4
8.2/10 Very Good! (1,001 reviews)
"Good"

Reviewed on May 16, 2024

Best Western O'Hare/Elk Grove Hotel
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 $119 per night from Jun 2 to Jun 3
$119
$152 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,002 reviews)
"Average"

Reviewed on May 12, 2024

Eaglewood Resort and Spa
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Fully refundable
The price is $98 per night from May 19 to May 20
$98
$111 total
includes taxes & fees
May 19 - May 20
8.4/10 Very Good! (1,001 reviews)
"Buen servicio y buen desayuno."

Reviewed on May 11, 2024

Hyatt Place Chicago/Hoffman Estates
See all 525 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.

Explore other types of vacation packages

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?
From as low as $564. Yes, you read that correctly. Our Sleepy Hollow packages are an easy way to stretch your budget further. Combine your preferred hotels, flights and rental car and get out and see this exciting destination.
How do I get a cheap travel package to Sleepy Hollow?
Bundle your hotels and flights with Expedia to save big bucks on your next big adventure. With more than 550 partner airlines and 1,000,000 hotels around the globe, your Sleepy Hollow vacation package can be tailored exactly to suit your travel style. With all that extra money, why not throw in one or two fun experiences and tours? It’s an easy way to unlock even more discounts. That dream vacation to Sleepy Hollow is closer than you thought!
Where should I stay in Sleepy Hollow?
A trip to Sleepy Hollow isn’t complete without stopping by Santas Village, Advocate Sherman Hospital and Randall Oaks Golf Club. Spend your nights close to these attractions and make sightseeing a breeze.
How far in advance should I book my Sleepy Hollow vacation?
Your best bet is to book early. Air carriers typically release flight tickets up to 12 months in advance, and this is your chance to score some of the lowest prices. Just been told you should take all your vacation days in a few weeks? That’s alright! Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Sleepy Hollow travel package include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to creating your Sleepy Hollow break, you’re in control!
What should I know before booking a Sleepy Hollow travel package?
So many places to explore, so many things to experience. With a travel package, you can check more of them off your list. Combine your hotels, rental cars and flights and land big savings.
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Yes, and with over 550 airlines to pick from worldwide, you’re spoiled for choice. Look through the available options and see which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
If your vacation plans in Sleepy Hollow have been upended, it’s good to know that it’s possible to cancel or amend your booking. If you made your booking in the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. To learn more, check our Customer Service Portal.

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