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Hotels recommended for families in Sleepy Hollow

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

Carleton of Oak Park

Oak Park

NT$4,337 total

includes taxes & fees

Oct 28 - Oct 29

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.

A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top Sleepy Hollow Hotel Reviews

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great location."

The Godfrey Hotel Chicago

8/10 Good

"The hotel was nice, and the location was great. However, the property could use a little updating and more attention to detail, especially with the bathroom amenities. The hallways were also quite noisy, with a lot of partying going on. I certainly don’t mind people having a good time, but it did get a bit loud. Overall, it was an okay stay, but I felt it was overpriced for what was offered. There were other hotels nearby at about the same price that appeared to be substantially nicer. Not a bad experience, just not quite worth the price."

Frequently asked questions

What's it like in Sleepy Hollow?

Sleepy Hollow is a neighborhood that travelers like for its restaurants.

If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?

Yes! The majority of hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.

Where can I learn more about changing or cancelling my trip to Sleepy Hollow?

For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.

What can I see and do in this Chicago neighborhood?

Douglas Park, Hawthorne Race Course, and Hawthorne Works Museum are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Jedlica Performing Arts Center and Los Globos are also worth a stop.

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Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. Hyatt House Chicago/West Loop-Fulton Market

3. Hampton Inn Chicago-O'Hare International Airport

4. Hilton Vacation Club Hotel Blake Chicago

5. Hyatt Regency Chicago

6. Hyatt Place Chicago/River North

7. Hotel Riu Plaza Chicago

8. L7 Chicago by LOTTE

9. LondonHouse Chicago, Curio Collection by Hilton

10. Embassy Suites by Hilton Chicago Downtown River North

11. Homewood Suites by Hilton Chicago Downtown South Loop

12. InterContinental Chicago Magnificent Mile by IHG

13. Radisson Blu Aqua Hotel Chicago

14. Residence Inn Chicago Downtown/Loop

15. The Emily Hotel

16. Hyatt Place Chicago/Downtown - The Loop

17. Hilton Chicago

18. Best Western Grant Park Hotel

19. Fairfield Inn & Suites Chicago Downtown/River North

20. The Royal Sonesta Chicago Downtown

Hotels recommended for families in Sleepy Hollow

Carleton of Oak Park

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

The Royal Sonesta Chicago Downtown

Frequently asked questions

Explore a world of travel with Expedia