Sleepy Hollow Holidays

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Things to do near Sleepy Hollow

Sleepy Hollow offers a delightful destination for outdoor family activities and city-themed vacations. Visitors can enjoy popular pastimes such as golfing at local courses and exploring recreational areas. Additionally, art galleries can be found in the vicinity, providing a cultural experience amidst the breathtaking scenery that the area has to offer.

Shopping

For a delightful shopping experience in Sleepy Hollow, visit Cabela's, just 8.0km away, for outdoor gear. The Arboretum of South Barrington, 9.7km away, offers a vibrant mix of shops. If you're up for a drive, Charlestowne Mall, located 19.3km away, features diverse shopping and entertainment options.

Recreation

At Makray Memorial Golf Club, enjoy a round of golf amidst scenic landscapes, perfect for both relaxation and sport. Moraine Hills State Park offers a serene environment for hiking and unwinding in nature, while Otter Cove Aquatic Park provides family-friendly aquatic fun in a vibrant atmosphere.

Adventure

Experience the thrill of North Wall Rock Climbing, located 12.9km from Sleepy Hollow, where you can challenge yourself in a vibrant outdoor setting. Explore the Algonquin Lakes Trailhead, a 6.4km trek that immerses you in nature, or hike the scenic Spring Lake Valley Forest Preserve Trailhead, 8.0km away.

Nightlife

In Sleepy Hollow, the nightlife buzzes with excitement at venues like Epic Air Trampoline Park and FireZone, both offering adventure-filled arcade experiences nearby. For a touch of romance and culture, the Hemmens Cultural Center provides captivating performances, creating a vibrant atmosphere for all visitors.

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

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

Booking tips and Expedia advantages for Sleepy Hollow

To save money on your trip to Sleepy Hollow, consider visiting between December and February when accommodation prices are lower. Booking your stay on a Monday can also help reduce costs, as Saturdays tend to be the most expensive. Utilise Expedia’s search tool to filter for budget-friendly hotels and explore eco-certified options for sustainable stays. Additionally, maximise your savings by bundling hotel reservations with flights and activities through package deals. For public transport, seek out affordable options to navigate the area and look for free local attractions to enhance your experience without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sleepy Hollow are December to February, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sleepy Hollow is Monday. The most expensive day to stay in Sleepy Hollow is Saturday.
  • Find cheap hotels on Expedia: Certainly. Here’s a paraphrased version in a trusted and attentive tone, using British English:Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Sleepy Hollow hotel reservation with your flights and activities through an Expedia package deal.

Top hotels in Sleepy Hollow

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 Rp1.486.926 per night from 23 Nov to 24 Nov
Rp1.486.926
Rp1.650.190 total
23 Nov - 24 Nov
includes taxes & fees
8/10 Very Good! (1,068 reviews)
Cooperative staff at front desk

Reviewed on 27 Oct 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is Rp971.542 per night from 27 Nov to 28 Nov
Rp971.542
Rp1.117.079 total
27 Nov - 28 Nov
includes taxes & fees
6.4/10 (1,018 reviews)
Great

Reviewed on 28 Oct 2025

Wyndham Garden Schaumburg Chicago Northwest
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 Rp1.849.923 per night from 9 Nov to 10 Nov
Rp1.849.923
Rp2.419.037 total
9 Nov - 10 Nov
includes taxes & fees
8.6/10 Excellent! (1,026 reviews)
100/10 recommend!
I stayed friday-sunday and I had to switch rooms on Saturday due to my tub filling up/backing up as I took a shower but they waived the entire resort fee so I'm still sticking to my word that everything was perfect, rooms were very clean and peaceful, it felt like home away from home and I'll definitely ...

Reviewed on 27 Oct 2025

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.