Sleepy Hollow Hotels: Cheap Accommodation in Sleepy Hollow

Q: How can I save on a hotel booking in Sleepy Hollow with Expedia?

One Key™ —Expedia’s free travel rewards programme—gives you instant access to discounts with Member Prices on Sleepy Hollow hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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Compare popular hotels in Sleepy Hollow

Property	Property class	Guest rating
Carleton of Oak Park	3.0 star property	9.2 Wonderful 1,209 reviews	View
Sable at Navy Pier Chicago, Curio Collection by Hilton	4.0 star property	9.4 Exceptional 2,761 reviews	View
Hyatt House Chicago/West Loop-Fulton Market	3.5 star property	9.0 Wonderful 1,316 reviews	View
Hilton Garden Inn Chicago Downtown South Loop	3.0 star property	8.8 Excellent 2,203 reviews	View
Le Méridien Essex Chicago	4.0 star property	9.0 Wonderful 1,003 reviews	View

Our guide on where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top Sleepy Hollow Hotel Reviews

Recent Reviews in Sleepy Hollow

Sports Illustrated Resorts Chicago

8/10 Good

"The hotel didn’t meet my expectations for the view, but it definitely had one of the best locations. The location was absolutely unbeatable, with easy walking access to Millennium Park, the Chicago Riverwalk, the Chicago Theatre, Art institute of Chicago and many other downtown attractions. It made exploring the city on foot incredibly convenient and enjoyable. The room was comfortable, and the overall atmosphere had a distinctive character. I especially appreciated being able to reach so many of Chicago’s highlights without having to rely on transportation. My only disappointment was the view, which fell short of what I had hoped for. However, the hotel’s prime location made up for much of that disappointment. Overall, it was a convenient and enjoyable place to stay for a few days in Chicago. I would recommend it to travelers who prioritize location and easy access to the city’s main attractions over a spectacular room view."

L7 Chicago by LOTTE

10/10 Excellent

"Have stayed at this hotel several times and always am very happy with staff and accommodations. It’s my favorite hotel in Chicago and I’ve stayed in many over the years. Maura (?) at front desk was helpful, professional and friendly. The cheerful concierge, Antonio, always is a pleasure and very helpful. Love the coffee in the lobby! Housekeeping does an exemplary job. Rooms here always are kept up, appearing newly furnished and extremely clean. I would prefer a larger fridge but rooms generally are nicely outfitted. I very much appreciate the attention to environmental issues, like bathroom cold water being filtered and drinkable. Location is great for me - not far from the Art Institute and a short taxi ride to the Lyric Opera. Sent from my iPhone"

Frequently asked questions

What are the best hotels in Sleepy Hollow that travellers recommend?

For hotels in Sleepy Hollow that travellers frequently recommend, consider the Carlton Inn Midway.

The Carlton Inn Midway is praised by guests for its excellent complimentary breakfast and its nice, clean rooms. The staff are often described as friendly and providing great customer service. This hotel offers premium bedding and air conditioning, ensuring a comfortable stay. Its location within a shopping district adds convenience for guests.

What are the best family hotels in Sleepy Hollow?

For a family-friendly hotel in Sleepy Hollow, the Carlton Inn Midway is a highly recommended option.

The Carlton Inn Midway offers a range of convenient amenities for families, including complimentary continental breakfast and free WiFi. Guests appreciate the free wired internet in public areas, and free self-parking is also available. For those travelling with infants, a free crib can be provided. The hotel also offers a complimentary 24-hour airport shuttle, making arrivals and departures straightforward. Guests frequently mention the excellent and free breakfast, along with the nice, clean rooms and friendly, great staff.

What hotels in Sleepy Hollow offer free breakfast?

For hotels in Sleepy Hollow that offer free breakfast, the Carlton Inn Midway is a highly recommended option.

The Carlton Inn Midway provides a complimentary breakfast, with guests frequently praising the excellent quality of the breakfast offerings. This hotel also offers free WiFi, free self-parking, and a 24-hour airport shuttle service, making it a convenient choice for travellers. Their rooms are often described as nice and clean, and the staff consistently receives commendations for being friendly and providing great customer service.

What are the top pet-friendly hotels in Sleepy Hollow?

For a top pet-friendly hotel in Sleepy Hollow, the Carlton Inn Midway is a great option.

The Carlton Inn Midway welcomes both dogs and cats. This hotel offers complimentary wired internet in public areas and free WiFi, along with a free continental breakfast and free self-parking. For added convenience, there is a 24-hour free airport shuttle and complimentary toiletries. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff.

What are the best budget hotels in Sleepy Hollow?

For budget-friendly accommodation in Sleepy Hollow, the Carlton Inn Midway is an excellent choice.

This hotel offers a range of convenient amenities, including free WiFi, complimentary continental breakfast, and free self-parking. Guests frequently mention the excellent and free breakfast, nice and clean rooms, and the friendly and great staff. For added convenience, the hotel provides a 24-hour free airport shuttle service and free toiletries.

When is the best time to go to Sleepy Hollow?

The best time to go to Sleepy Hollow, Illinois, is during the autumn months, particularly from late September to late October.

This period offers pleasant weather, with mild temperatures and colourful foliage, making it ideal for outdoor activities and exploring the area. The days are generally sunny, providing comfortable conditions for walks and visits to local attractions.

For families, visiting in October is particularly good due to the many Halloween-themed events and activities that take place. These often include pumpkin patches, corn mazes, and special community gatherings that are very popular with children and offer a memorable holiday experience.

Couples looking for a relaxing escape will also appreciate the autumn.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our 'Fully refundable property' filter during your search to find the right Sleepy Hollow hotel for you.

How can I save on a hotel booking in Sleepy Hollow with Expedia?

One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Sleepy Hollow hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Sleepy Hollow?

Hotel prices in Sleepy Hollow often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by 'Price: low to high' for our cheapest rates.

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Sleepy Hollow Hotels, Chicago

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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. Best Western Grant Park Hotel

4. Hilton Garden Inn Chicago Downtown South Loop

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. Sable at Navy Pier Chicago, Curio Collection by Hilton

7. Hyatt Place Chicago/Downtown - The Loop

8. Crowne Plaza Chicago West Loop by IHG

9. Hilton Vacation Club Hotel Blake Chicago

10. Hampton Inn Chicago West Loop Fulton Market Area

11. Hampton Inn & Suites Chicago Downtown

12. Le Méridien Essex Chicago

13. Level Chicago Fulton Market

14. citizenM Chicago Downtown

15. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

16. Holiday Inn Chicago Dwtn - The Mart by IHG

17. Cambria Hotel Chicago Loop - Theatre District

18. Aloft by Marriott Chicago Mag Mile

19. DoubleTree by Hilton Chicago - Magnificent Mile

20. La Quinta Inn & Suites by Wyndham Chicago Downtown

Compare popular hotels in Sleepy Hollow

Our guide on where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Recent Reviews in Sleepy Hollow

Sports Illustrated Resorts Chicago

Frequently asked questions

Explore a world of travel with Expedia