Chestertown Vacation Packages

Now's the time to design your perfect Chestertown escape. Take a load off, relax and let the expert crew at Orbitz find the best-value flight and hotel deals for you. Imagine all the extra things you can do with savings of as much as . Simply pick your preferred hotels, airfares, rental cars and experiences to save cash! And that's not all — if you're wondering where to stay or who to fly with, our ever-expanding database has 500,000 hotels worldwide and 500 partner airlines. The choice is yours! There are endless possible options to craft your own remarkable vacation, no matter your style, budget or needs.

Where is Chestertown?

So, you've been told Chestertown is an awesome place to visit? Racking your brains trying to remember where it is? Let us point you in the right direction. This city is approximately 25 miles northeast of the capital of Maryland, Annapolis. Chestertown is also 18 miles southeast of Edgewood. This corner of Eastern Shore is home to around 5,000 people, some of whom will surely be happy to give you some travel tips.

Car Rentals in Chestertown

Take your love of travel further by checking out car rentals in Chestertown. No matter where you go or what you'd like to do, Orbitz will help you find a ride that satisfies your adventurous spirit. Collect your car from Hertz at Baltimore Washington International Thurgood Marshall Airport and you can go directly from the tarmac to the highway. Is your accommodation in town? Start your adventure on a high by beginning your trip from the middle of the city. You'll find Enterprise situated at 121 Flatland Rd.

Where to stay in Chestertown – Hotel Accommodation

Currently, Orbitz only lists 4 hotels in Chestertown. If you're eager to stay the night, reserve your room soon. We'll try to make arranging your trip simple and easy. Recommended hotels include the Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

Nearest Airports to Chestertown

If you're flying in to Chestertown, you'll likely be arriving at Baltimore Washington International Thurgood Marshall Airport (BWI). Grab a coffee and get your bearings after climbing out of the plane. This is the nearest airport, sitting 30 miles from the downtown area.

Popular Places to Visit Near Chestertown

Chestertown has plenty of things to keep you busy, but if you're wanting to explore further afoot, you're in luck! You've got renowned attractions just a stone's throw from here! 50 miles away is Cheverly. Many visitors use this locality as a base to visit the world-renowned attraction, United States Capitol.

No Cancellation Fees

We're aware that even the best-laid plans can change. So, if you have to change or cancel your bookings you will not get a fee from us.^ If you act fast, your selected airline or hotel might not charge you either.