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Our top choices for Sleepy Hollow hotels

FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
3.0 star property
River North, 7.8 mi from Sleepy Hollow
6.8 out of 10, (11 reviews)
"Overall was a good stay!! Wish the place next door wasn’t as loud at night."
United States
Lia
$156 nightly
The price is $183
Jul 26 - Jul 27
Total with taxes and fees
FOUND Hotels, Chicago, Series by Marriott

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 8.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,605 reviews)
"View was beautiful, accommodations were excellent."
United States
Julie
$277 nightly
The price is $329
Aug 9 - Aug 10
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 7.5 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,529 reviews)
"Staff was very nice. Hotel is beautiful "
United States
Britney Q
$241 nightly
The price is $287
Aug 9 - Aug 10
Total with taxes and fees
Palmer House a Hilton Hotel

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 7.6 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,277 reviews)
"Wonderful stay"
United States
Taylor
$203 nightly
The price is $242
Aug 9 - Aug 10
Total with taxes and fees
Silversmith Hotel Chicago Downtown

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 8 mi from Sleepy Hollow
7.8 out of 10, Good, (3,197 reviews)
"Great location."
United States
Clifton
$144 nightly
The price is $171
Aug 10 - Aug 11
Total with taxes and fees
Freehand Chicago

LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (169 reviews)
"Clean, new, and cozy stay in a great location."
United States
Pedro
$164 nightly
The price is $193
Jul 19 - Jul 20
Total with taxes and fees
LIVN - West Loop Chicago

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 7.3 mi from Sleepy Hollow
7.6 out of 10, Good, (2,710 reviews)
"Excellent hotel and services"
United Kingdom
Marobe
$170 nightly
The price is $202
Aug 10 - Aug 11
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago

The Wade

The Wade
4.5 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,927 reviews)
"Great stay and friendly staff!"
Canada
Richard
$254 nightly
The price is $302
Aug 9 - Aug 10
Total with taxes and fees
The Wade

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 8.7 mi from Sleepy Hollow
8.2 out of 10, Very Good, (1,747 reviews)
"Nice place to stay"
Australia
Anna
$163 nightly
The price is $193
Jul 27 - Jul 28
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,332 reviews)
"I liked the ambiance of the hotel, everyone was nice and it was very clean."
United States
Tanil
$186 nightly
The price is $221
Aug 10 - Aug 11
Total with taxes and fees
The Godfrey Hotel Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 7.4 mi from Sleepy Hollow
8.0 out of 10, Very Good, (10,262 reviews)
"We’ve stayed there twice and probably will again."
United States
Ashley
$210 nightly
The price is $250
Aug 10 - Aug 11
Total with taxes and fees
Congress Plaza Hotel

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,035 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
$207 nightly
The price is $246
Aug 12 - Aug 13
Total with taxes and fees
Warwick Allerton - Chicago

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 7.7 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,042 reviews)
"Love the location and top tier service"
United States
Christine
$253 nightly
The price is $300
Jul 26 - Jul 27
Total with taxes and fees
theWit Chicago, a Hilton Hotel

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 7.6 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,147 reviews)
"Beautiful historic building; dog friendly!"
United States
Zoe
$233 nightly
The price is $277
Aug 9 - Aug 10
Total with taxes and fees
Staypineapple, An Iconic Hotel, The Loop

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.4 mi from Sleepy Hollow
7.8 out of 10, Good, (1,751 reviews)
"Nice and comfortable place to stay"
Australia
Precious
$162 nightly
The price is $192
Aug 4 - Aug 5
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 7.2 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (1,281 reviews)
"Comfortable hotel in a good location. Lots of public transportation close."
United States
Dean
$183 nightly
The price is $218
Aug 9 - Aug 10
Total with taxes and fees
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,804 reviews)
"Beautiful hotel and location. Staff were very friendly and kind."
Canada
Sophie
$249 nightly
The price is $296
Aug 9 - Aug 10
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 7.2 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,027 reviews)
"Wonderful stay…very well located"
United States
Kathleen
$239 nightly
The price is $284
Aug 14 - Aug 15
Total with taxes and fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 7.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (3,597 reviews)
"Great hotel for stay in The Loop, close to everything."
United States
Héctor
$185 nightly
The price is $220
Aug 9 - Aug 10
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3,741 reviews)
"Nice place great staff and a great location"
United States
Byron
$200 nightly
The price is $238
Aug 9 - Aug 10
Total with taxes and fees
Eurostars Magnificent Mile
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.

Where to stay in Sleepy Hollow

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

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.

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.

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.

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.

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.

Top Sleepy Hollow Hotel Reviews

Frequently asked questions

What other neighbourhoods are similar to Sleepy Hollow?
Sleepy Hollow is a suburban village, so other similar areas would be the surrounding towns in the Fox River Valley like West Dundee, East Dundee, and Carpentersville.

West Dundee, located just south of Sleepy Hollow along the Fox River, offers a similar quiet, residential feel with a charming downtown area. This area is great for families looking for a relaxed atmosphere with local parks and community events, and it provides easy access to the river for outdoor activities.

East Dundee, situated across the Fox River from West Dundee, also provides a comparable suburban experience. It features a mix of residential streets and a small, established downtown with local shops and eateries.
What are the best hotels in Sleepy Hollow that travelers recommend?
For a highly recommended hotel in Sleepy Hollow, consider the Carlton Inn Midway.

The Carlton Inn Midway offers a comfortable stay with amenities that guests appreciate. Travelers frequently mention the excellent and free continental breakfast as a highlight, along with the nice and clean rooms. The staff also receives high praise for their friendly and great customer service. The hotel provides air conditioning and premium bedding, ensuring a pleasant and restful experience.
What are the best family hotels in Sleepy Hollow?
For family-friendly hotels in Sleepy Hollow, the Carlton Inn Midway is a highly recommended option.

This hotel offers a range of convenient amenities for families, including complimentary breakfast and free wired internet in public areas. Travelers appreciate the free airport shuttle available 24 hours a day, as well as complimentary self-parking. The hotel also provides free toiletries and free WiFi. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff and customer service.
What hotels in Sleepy Hollow offer free breakfast?
For a hotel in Sleepy Hollow that offers free breakfast, consider the Carlton Inn Midway.

The Carlton Inn Midway provides complimentary breakfast, including continental options, which guests frequently describe as excellent. This hotel also offers a 24-hour free airport shuttle, free self-parking, and free wired internet in public areas, adding to its convenience. Guests consistently praise the clean rooms and the friendly, great staff.
What are the top pet-friendly hotels in Sleepy Hollow?
For a top pet-friendly hotel in Sleepy Hollow, consider the Carlton Inn Midway.

The Carlton Inn Midway welcomes both dogs and cats, making it an ideal choice for travelers with pets. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff. This hotel also offers a complimentary 24-hour airport shuttle, free wired internet in public areas, and free self-parking, adding to its convenience.
What are the best budget hotels in Sleepy Hollow?
For a budget-friendly stay in Sleepy Hollow, the Carlton Inn Midway is an excellent option.

This hotel offers a range of complimentary amenities that enhance its value, including free wired internet in public areas, free breakfast, and free continental breakfast. Guests also benefit from a free airport shuttle service available 24 hours a day and free self-parking. Travelers often praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff, highlighting the quality of customer service.
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 and allows visitors to fully experience the area's seasonal offerings.

Autumn in Sleepy Hollow aligns perfectly with events and attractions related to the famous legend. Travelers seeking a festive and atmospheric experience will find the crisp air and fall foliage enhance the local activities, from pumpkin patches to corn mazes. Couples looking for a cozy getaway will appreciate the picturesque surroundings and themed events.

For families, visiting during this time provides ample opportunities for seasonal fun. Many local farms and community centers host family-friendly events with hayrides and apple picking, providing entertainment for all ages.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sleepy Hollow.
How can I save on a Sleepy Hollow hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and 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.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Sleepy Hollow hotel?
Prices for hotels in Sleepy Hollow often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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