Visit Sleepy Hollow: 2026 Travel Guide for Sleepy Hollow, Illinois

Eaglewood Resort and Spa

1401 Nordic Rd Itasca IL

$158 nightly

$176 total

Oct 11 - Oct 12

Total with taxes and fees

Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...

8.8/10 Excellent! (1,350 reviews)

"great stay such a shame we had no kicrowave tho."

Reviewed on Sep 20, 2026

Hyatt Regency Schaumburg Chicago

1800 East Golf Rd Schaumburg IL

$139 nightly

$160 total

Oct 17 - Oct 18

Total with taxes and fees

Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

1200 N Mittel Blvd Wood Dale IL

$123 nightly

$137 total

Oct 5 - Oct 6

Total with taxes and fees

Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...

7.8/10 Good! (1,050 reviews)

"We had great experiences here. But last night, there were stains all over our bed, and the room wasn’t even vacuumed…. There was no breakfast buffet. It just wasn’t a good experience.. especially celebrating our anniversary."

Reviewed on Sep 20, 2026

See all 494 properties in Sleepy Hollow

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.

Pet Friendly, Near O’Hare, Fenced in, Cheerful Frida & Diego Home, up to 6 ppl

Wood Dale IL

Stay at this vacation home in Wood Dale. Enjoy a garden, laundry facilities, and patios. Popular attractions Addison Ice Arena and Pirates Cove Childrens Theme ...

10/10 Exceptional! (21 reviews)

"Property was great for us and our 2 dogs. Property is well-maintained and owner was easy to work with."

Reviewed on Sep 7, 2026

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Schaumburg IL

Stay at this vacation home in Schaumburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woodfield Mall and The Chicago Athenaeum are ...

9.8/10 Exceptional! (47 reviews)

"The property was located perfectly to get around town. House was clean and well maintained. Host was very quick to respond to any of my questions or concerns. I’d highly recommend this home."

Reviewed on Aug 29, 2026

Spacious open concept home w/ game room + firepit

Winfield IL

Book a stay at this family-friendly vacation home in Winfield. Enjoy a garden, laundry facilities, and patios. Popular attractions DuPage Event Center & Fairgrounds ...

9.8/10 Exceptional! (99 reviews)

"Communication with host was the best! Planned this trip for a family wedding at Cantigny well in advance…home lived up to all of the good reviews I read! Highly recommended!"

Reviewed on Aug 24, 2026

See all properties in Sleepy Hollow

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.

Frequently asked questions

When is the best time to visit Sleepy Hollow?

The best time to visit Sleepy Hollow is from May through September, when the weather is generally pleasant for exploring. For fewer crowds and better value, the quieter months of December through March are a good bet, offering a cooler experience, potentially with snow.

What cuisines can you find in Sleepy Hollow?

In Sleepy Hollow you can find Caribbean cuisine, offering dishes such as jerk chicken, rice and peas, and plantains. Travelers can also enjoy a variety of other dining experiences, including Latin American, Italian, Asian, European, and North American options.

Can I book a refundable hotel in Sleepy Hollow?

Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Sleepy Hollow by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.

Why book a trip to Sleepy Hollow with Expedia?

Expedia makes it easier to plan your Sleepy Hollow trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.

Should I stay in a hotel or vacation rental in Sleepy Hollow?

The best choice depends on your travel style. Hotels in Sleepy Hollow can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.

How can I manage my Sleepy Hollow trip on Expedia?

Once you've booked your Sleepy Hollow trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.

What if I need help during my Sleepy Hollow trip?

Expedia offers customer support before, during, and after your Sleepy Hollow trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.

How can Expedia help me plan my first trip to Sleepy Hollow?

If it's your first trip to Sleepy Hollow, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.

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

Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Sleepy Hollow hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Sleepy Hollow, IL

Travel Guide