Sleepy Hollow Holidays from £1,241

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Your Sleepy Hollow Holiday

Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow holiday package. And with the ability to customise your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. Grand Victoria Casino, Santas Village and NOW Arena are among the top attractions worth exploring. Whatever your travel plans or budget, organising your ultimate tailored Sleepy Hollow holiday is simple with Expedia.

Top Sleepy Hollow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Swissotel - Chicago
Wyndham Garden Elk Grove Village/O'Hare
Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Schiller Park, IL - Chicago O'Hare

Things to do near Sleepy Hollow

Sleepy Hollow is perfect for family-friendly, outdoor, and city-themed holidays. Visitors can enjoy a variety of activities, including exploring shopping centres, educational attractions, and seasonal events. Key highlights include Halloween night festivities, live music performances, exciting new attractions, and fun tours that cater to all ages, ensuring a memorable experience for everyone.

Shopping

For a delightful shopping experience in Sleepy Hollow, visit Cabela's, only 8.0km away, for outdoor gear. The Crystal Court Shopping Center offers entertainment and family vibes, located 14.5km from town. If you're up for a drive, the Arboretum of South Barrington is 9.7km away, featuring diverse shopping options.

Recreation

Enjoy a cinematic experience at The Catlow Theater, where you can catch a film in a charming setting perfect for families and romance. For outdoor enthusiasts, the Randall Oaks Golf Club offers a delightful golfing experience amidst beautiful landscapes. Don't miss the Hemmens Cultural Center for a taste of local culture and entertainment.

Adventure

Explore the Algonquin Lakes Trailhead, a scenic trail located 6.4km from Sleepy Hollow, perfect for outdoor enthusiasts. For a picturesque hike, visit the Spring Lake Valley Forest Preserve Trailhead, situated 8.0km away, offering breathtaking views. For family fun, enjoy the Epic Air Trampoline Park, located 12.9km from Sleepy Hollow.

Nightlife

In Sleepy Hollow, enjoy a relaxed evening at The Village Squire, known for its hearty meals and lively atmosphere. For a more laid-back vibe, unwind at the local pub, The Sleepy Hollow Tavern, where you can savour a pint and engage in friendly conversation with locals.

*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, offers a delightful blend of family-friendly activities and outdoor adventures, making it perfect for a city-themed getaway. Explore local attractions such as event venues, urban parks, and nature reserves that cater to cultural and outdoor enthusiasts. Don't miss a visit to the historic Sleepy Hollow Cemetery for a unique experience. Embrace the charm of this quaint area while enjoying its diverse points of interest.

  • Woodstock Square: A charming square located 27.4km from Sleepy Hollow, Woodstock Square offers a delightful mix of city vibes and historic charm. Stroll through its quaint shops and cafes, and soak in the community atmosphere that has made it a local favourite.
  • Heritage Park: Situated 25.7km away, Heritage Park is an urban oasis perfect for families. Enjoy its vast green spaces and outdoor activities, making it an ideal spot for picnics, leisurely walks, and bonding with nature in a city setting.
  • Santa's Village: Just 3.2km from Sleepy Hollow, Santa's Village is a whimsical theme park filled with family-friendly entertainment. Experience festive rides and attractions that bring the magic of Christmas to life all year round.

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.

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
3,300
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Santas Village, Hemmens Cultural Centre and Epic Air Trampoline Park

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 £44 per night from 15 May to 16 May
£44
15 May - 16 May
includes taxes & fees
5.4/10 (1,004 reviews)
Worst place I’ve ever seen in my life. I did NOT stay here and they won’t refund either. Would definitely advise to stay far far away.

Reviewed on 23 Apr 2026

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
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 £101 per night from 10 May to 11 May
£101
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (1,036 reviews)
Enjoyed my stay. Loved the balcony.

Reviewed on 20 Apr 2026

Eaglewood Resort and Spa
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
Fully refundableReserve now, pay when you stay
The price is £87 per night from 1 May to 2 May
£87
1 May - 2 May
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Nice location and huge building, an clean room. But it is currently being renovated, so the public areas are mostly inaccessible.

Reviewed on 20 Apr 2026

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.