Sleepy Hollow Holiday Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Sleepy Hollow holiday rentals

Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Cottage in St. Charles

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
The price is S$694
includes taxes & fees
4 Jan - 5 Jan, 2026
Fire Pit & Grill: Family Home on Fox River Trail!
Room
King bed Crystal Lake Mchenry Cary Cozy

Holiday Home in Cary

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
The price is S$498
includes taxes & fees
11 Jan - 12 Jan, 2026
King bed Crystal Lake Mchenry Cary Cozy
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.
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Top Sleepy Hollow Hotel Reviews

Comfort Inn & Suites Geneva - West Chicago

Comfort Inn & Suites Geneva - West Chicago

10/10 Excellent
"Friendly staff, comfy bed and good breakfast. "
Debra 3-night trip
Posted 15 hours ago
Comfort Inn & Suites Geneva - West Chicago

Frequently asked questions

Are there holiday rentals in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. Sleepy Hollow is known for its bars.

What’s there to see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Santa's Village, or get outside and enjoy nature at Three Oaks Recreation Area. In the wider area, you’ll find Hemmens Cultural Center and Grand Victoria Casino.

What’s a holiday rental in Sleepy Hollow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sleepy Hollow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.