Hotels in Sleepy Hollow

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Nov 9 - Nov 10
Tonight
Check prices in Sleepy Hollow for tonight, Nov 9 - Nov 10
Nov 10 - Nov 11
Tomorrow night
Check prices in Sleepy Hollow for tomorrow night, Nov 10 - Nov 11

Featured Hotels in Sleepy Hollow

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.39 mi from Sleepy Hollow
$102 nightly
The price is $120 total per night
$120 total
Nov 10 - Nov 11
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.51 mi from Sleepy Hollow
$135 nightly
The price is $154 total per night
$154 total
Nov 24 - Nov 25
Total with taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, access to locker space, and luggage storage. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.86 mi from Sleepy Hollow
$114 nightly
The price is $134 total per night
$134 total
Nov 10 - Nov 11
Total with taxes and fees
At citizenM Chicago Downtown, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include coffee/tea in a common area, a computer station, and express check-in.
Free WiFi
Restaurant
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.98 mi from Sleepy Hollow
$94 nightly
The price is $110 total per night
$110 total
Dec 7 - Dec 8
Total with taxes and fees
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Additional amenities include meeting rooms, express check-out, and a porter/bellhop.
Pool
Pet friendly
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.01 mi from Sleepy Hollow
$108 nightly
The price is $127 total per night
$127 total
Dec 8 - Dec 9
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.03 mi from Sleepy Hollow
$81 nightly
The price is $96 total per night
$96 total
Dec 10 - Dec 11
Total with taxes and fees
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include express check-out, laundry facilities, and an ATM.
Pet friendly
Free WiFi
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.31 mi from Sleepy Hollow
$98 nightly
The price is $114 total per night
$114 total
Nov 26 - Nov 27
Total with taxes and fees
Guests of Aloft Chicago Mag Mile have access to an indoor pool, a gym, and free WiFi in public areas. Valet parking is offered for USD 65 per night. The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include conference space, a business center, and a microwave in a common area.
Pool
Pet friendly
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.41 mi from Sleepy Hollow
$92 nightly
The price is $108 total per night
$108 total
Nov 23 - Nov 24
Total with taxes and fees
The Whitehall Hotel, BW Premier Collection features a gym, free WiFi in public areas, and a business center. Self parking is offered for USD 56 per night. The 24-hour front desk has staff standing by to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this boutique hotel include a meeting room, a computer station, and free newspapers.
Breakfast included
Pet friendly
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.58 mi from Sleepy Hollow
$101 nightly
The price is $119 total per night
$119 total
Dec 7 - Dec 8
Total with taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and an ATM.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Sleepy Hollow
View all properties
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.
Sleepy Hollow Hotels

Orbitz makes it easy to find the best Sleepy Hollow hotel deals for your trip. With an outstanding selection, easy-to-use search tools and descriptive hotel profiles, you'll find Sleepy Hollow hotel deals in a wink..

Great selection of hotels in Sleepy Hollow

Whether you're searching for hotels in Sleepy Hollow on business, or hunting for a family getaway, Sleepy Hollow hotel options are only a click away. Find hotels in Sleepy Hollow with the location, star-rating and facilities you need. Narrow your search results even further by star rating, hotel chain and amenities, such as free parking, babysitting services, or fitness centers. And with area maps, you can view Sleepy Hollow hotels close you are to the airport and nearby attractions.

Sleepy Hollow hotel reviews, photos and virtual tours

Thanks to photos and virtual tours, you can look before you book your Sleepy Hollow hotel reservation. Check out Sleepy Hollow hotel properties using interactive tools which allow you view hotel rooms, common areas and key features. On Orbitz, you can also learn more about hotels in Sleepy Hollow with unbiased reviews from verified Sleepy Hollow hotel guests. We ask guests to offer candid feedback on services, comfort, location, value and amenities.

Grab Sleepy Hollow hotel deals and special offers

Orbitz works around the clock to find exclusive offers and Sleepy Hollow hotel deals, just for you. Sign up for deals by e-mail where you'll get first crack at money-saving extras like promo codes, resort credits, free nights and more. You can also "Like" Orbitz on Facebook and follow us on Twitter to receive up-to-the-minute news on hotel discounts, giveaways and more.

24/7 support with Sleepy Hollow hotel reservations

When it comes to finding hotels in Sleepy Hollow, an Orbitz specialist can help you find the property right for you. Chat live or call 1-800-454-3743 any time for help booking your hotels in Sleepy Hollow. Our team of experts can help you pinpoint Sleepy Hollow hotels options suited to your tastes and budget.

Forget Orbitz change or cancel fees on Sleepy Hollow hotels

On Orbitz, Sleepy Hollow hotel deals mean flexibility. If you need to change your Sleepy Hollow hotel reservations, or cancel your stay, Orbitz doesn't charge cancel or change fees. Orbitz also offers great selection on airline tickets, vacation packages, and car rental deals to so you can plan your trip to Sleepy Hollow all in one place.

 

Sleepy Hollow hotels essential information

Accommodation
4,824 hotels
Lowest Price
$96
Highest Price
$154
Popular hotels
Embassy Suites by Hilton Chicago Downtown River North, Congress Plaza Hotel, Hilton Chicago/Magnificent Mile Suites, Hilton Garden Inn Chicago Downtown/Magnificent Mile, citizenM Chicago Downtown, Freehand Chicago, Aloft Chicago Mag Mile, Palmer House a Hilton Hotel, The Whitehall Hotel, BW Premier Collection

Popular places to visit

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

See properties in Wrigley Field
Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

See properties in Michigan Avenue
Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.

See properties in Navy Pier
Navy Pier

Recent Reviews

Congress Plaza Hotel

Congress Plaza Hotel

5/5 Excellent
"a"
A verified traveler stayed at Congress Plaza Hotel
Posted 17 hours ago
Congress Plaza Hotel

More to Explore