Sleepy Hollow Holidays

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The Annual Holiday Sale

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Things to do near Sleepy Hollow

Sleepy Hollow is perfect for family-friendly outdoor adventures and urban exploration. Visitors can enjoy various activities, including shopping at local centres, attending live music events, and exploring new attractions. Don't miss out on the festive Halloween night celebrations and seasonal attractions that add to the charm of this quaint destination. Fun tours are also available, ensuring an enjoyable experience for all ages.

Shopping

Cabela's, located 8.0km from Sleepy Hollow, offers a fantastic selection of outdoor gear and gifts. If you're up for a drive, Charlestowne Mall and Village Square Shopping Center, both 19.3km away, provide a vibrant mix of shopping, dining, and entertainment for the whole family.

Recreation

The Arcada Theater, located 20.9km from Sleepy Hollow, offers a captivating blend of romance and culture through its diverse performances. Similarly, the Steel Beam Theater, also 20.9km away, provides a charming atmosphere for family entertainment. For a more local experience, Cinemark West Dundee, just 483m away, is perfect for a family movie outing.

Adventure

Experience the thrill of Epic Air Trampoline Park, located 12.9km from Sleepy Hollow, where you can bounce around in an exciting arcadeAdventureZone. For nature lovers, the scenic Spring Lake Valley Forest Preserve Trailhead, 8.0km away, offers picturesque hiking trails, while Algonquin Lakes Trailhead, 6.4km away, beckons with its outdoor adventure vibes.

Nightlife

Sleepy Hollow boasts a quaint yet vibrant nightlife. Visit The Village Squire for hearty pub fare and a warm atmosphere. For a laid-back evening, enjoy craft beers at the nearby Sleepy Hollow Brewing Company, where local musicians often perform, creating a cheerful ambience for all.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Sleepy Hollow

Sleepy Hollow, Illinois, is an ideal destination for families and outdoor enthusiasts, offering a delightful mix of urban parks, event venues, and nature reserves. Visitors can immerse themselves in local culture while exploring attractions like the Sleepy Hollow Cemetery. This charming locale promises a memorable experience for all types of travellers seeking a blend of relaxation and adventure in a picturesque setting.

  • Fox River Preserve: Located 17.7km from Sleepy Hollow, this park offers a serene escape into nature. With its eco-friendly atmosphere, visitors can enjoy family-friendly activities such as hiking, birdwatching, and picnicking amidst beautiful landscapes along the Fox River.
  • Santa's Village: Just 3.2km away, this enchanting theme park is perfect for families seeking fun and entertainment. With festive rides, engaging attractions, and seasonal events, Santa's Village brings the magic of Christmas to life all year round.
  • NOW Arena: Situated 8.0km from Sleepy Hollow, this entertainment facility hosts exciting events and performances. Families can enjoy thrilling sports matches, concerts, and various shows, making it a vibrant hub for local entertainment.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sleepy Hollow falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Sleepy Hollow falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.3°F (-5.4°C)Light RainMostly CloudySlightly LowSlightly Low
February24.6°F (-4.1°C)Light RainMostly CloudySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly CloudyAverageAverage
April47.3°F (8.5°C)Light RainMostly CloudyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnySlightly HighSlightly High
July72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnySlightly HighSlightly High
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowSlightly Low

Tips to save on your trip to Sleepy Hollow

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Sleepy Hollow during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Sleepy Hollow

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

2 out of 5
22 West Algonquin Road Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is S$69 per night from 19 Feb to 20 Feb
S$69
19 Feb - 20 Feb
includes taxes & fees
5.4/10 (1,004 reviews)
Other than the Roaches everything was great! A few bugs can't beat the deal I got.

Reviewed on 10 Feb, 2026

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
2112 S Arlington Heights Rd Arlington Heights IL
The price is S$113 per night from 16 Feb to 17 Feb
S$113
16 Feb - 17 Feb
includes taxes & fees
8.2/10 Very Good! (995 reviews)
Great service and rooms

Reviewed on 31 Jan, 2026

Comfort Inn & Suites Arlington Heights - Schaumburg
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 28 Feb to 1 Mar
S$169
28 Feb - 1 Mar
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Everything was great

Reviewed on 6 Feb, 2026

Eaglewood Resort and Spa
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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