Sleepy Hollow Vacations from $385
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Your Sleepy Hollow Vacation
Experience everything this neighborhood has to offer with a tailor-made Sleepy Hollow vacation package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow vacation into reality, whatever your travel plans or budget.
The Latest Sleepy Hollow Vacation Packages
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Reviewed on Oct 2, 2026
Where to stay in 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.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"
Reviewed on Oct 3, 2026
Things to do
