Sleepy Hollow, IL

Travel Guide

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
$163 nightly
The price is $181 total per night from Oct 25 to Oct 26
$181 total
Oct 25 - Oct 26
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 ...
Eaglewood Resort and Spa
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd Schaumburg IL
$127 nightly
The price is $146 total per night from Oct 11 to Oct 12
$146 total
Oct 11 - Oct 12
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 ...
Hyatt Regency Schaumburg Chicago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd Wood Dale IL
$107 nightly
The price is $119 total per night from Nov 1 to Nov 2
$119 total
Nov 1 - Nov 2
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 ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
See all 499 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

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 390 Golf Experience and Addison Ice Arena are located ...
10/10 Exceptional! (22 reviews)
"Wonderfully unique property. Felt cozy and like a home away from home."

Reviewed on Sep 11, 2026

Pet Friendly, Near O’Hare, Fenced in, Cheerful Frida & Diego Home, up to 6 ppl
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

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! (49 reviews)
"Location & home were perfect for us. All of the rooms were very clean. Home is situated in a quiet and well kept neighborhood. Parking was ideal for our group. The host (Gergana) answered all of our ?'s and concerns and was an excellent host! The only issue we had is the Master Bathroom where the ..."

Reviewed on Oct 1, 2026

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Spacious open concept home w/ game room + firepit

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! (100 reviews)
"Our family had a great time staying in this location! It was a blessing for our children to be able to come and celebrate the wedding of our youngest son. I would love to come back another time."

Reviewed on Sep 7, 2026

Spacious open concept home w/ game room + firepit
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.

Cities near Sleepy Hollow

A river with a bridge, a park, and buildings along the riverbank.

Elgin

A residential street lined with autumn-colored trees and houses.

West Dundee

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