Hotels in Sleepy Hollow

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Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Where to stay in Sleepy Hollow?

When is the best time to visit Chicago?

Our prices for hotels in Chicago are cheapest in January
Price trends for hotels in Chicago
Pricing is based on two traveller single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Chicago
December
High crowds
High 3°C / low -2°C. Cloudy most days.
View properties in December
3°
weather_cloudy
December, High crowds, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
-1°
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January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
0°
ac_unit
February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
6°
weather_cloudy
March, Low crowds, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
11°
weather_partly_sunny
April, Low crowds, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
17°
weather_sun
May, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
23°
weather_sun
June, High crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
26°
weather_sun
July, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
26°
weather_sun
August, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
23°
weather_sun
September, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
16°
weather_sun
October, Moderate crowds, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
8°
weather_partly_sunny
November, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
Monthly weather averages (˚C)

Check out reviews of Sleepy Hollow hotels guests love

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Room was clean, staff amazing and just an overall great place to stay. "
Jerome 2-night trip
Posted 6 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Frequently asked questions

Is Sleepy Hollow expensive to stay in?
You can find great hotels from ฿2,731 in Sleepy Hollow to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Sleepy Hollow hotels?
Discover great deals on hotels in Sleepy Hollow with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Sleepy Hollow hotels.
How can I find discounted rates and deals for Sleepy Hollow hotels?
Unlocking discounted rates at hotels in Sleepy Hollow couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Sleepy Hollow hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Sleepy Hollow hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
Is it worth staying in Sleepy Hollow?
Basing yourself in Sleepy Hollow makes it easy to explore Chicago, including the areas of Near West Side and Lawndale.
Find out more about Sleepy Hollow

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