Sleepy Hollow Vacation Packages for 2026

Sleepy Hollow Vacation Packages

Trying to save both time and money on your upcoming holiday to Sleepy Hollow? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Sleepy Hollow the best one yet. With only a few clicks, you can pick the best Sleepy Hollow vacation package for you. We have a fabulous choice of flights and hotels, and Sleepy Hollow endeavors to choose from.

Sleepy Hollow Hotels

Our listings include lodgings that are close to all the Sleepy Hollow points of interest, and some that are just outside the city center for a more restful retreat.

Check out the verified hotel reviews on the AARP Travel Center to help you decide.
• It will be easy to choose a fabulous hotel, as a number of accommodations in Sleepy Hollow have a perfect overall rating of 5 stars
• You should have no issues taking it easy after a busy day, as these hotels have a perfect 5 star rating for room comfort.
• With a solid 3 rating, you know that you'll be greeted with a clean room when you return from exploring Sleepy Hollow
• The immaculate grounds of the area's hotels also got sky-high marks

Thanks to AARP Travel Center's Sleepy Hollow hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Sleepy Hollow

Sleepy Hollow is home to around 2,720,550 people, so you know there will be a lot to do no matter who you are. With this area's burgeoning art scene, local attractions, and a rich past that is a beacon for history buffs, you may have a hard time fitting everything into one trip. There are a large number of worthwhile things to do and see in and around Sleepy Hollow that can help make your trip a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:

• Grant Park and Buckingham Fountain
• Museum of Science and Industry
• Shedd Aquarium
• Chicago Architecture River Cruise

If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.

Book Together and Save

As an AARP Member, you can take advantage of all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what vacation package you pick, your membership savings helps you get a great deal. So what are you waiting for? Bundle now and get ready for your Sleepy Hollow vacation.