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.
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.
You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
Notable for its university life, Chestertown features attractions such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. The city has something for everyone including sights like Garfield Center for the Arts at the Prince Theater and Chestertown Historic District within a small-town setting.
The town is absolutely charming, a cozy little jewel of the Chesapeake. The Tea Party is underrated, a definite must do for Memorial Day weekend. The fair is fraught with great food, drink, entertainment, and of course, the A+ colonial swashbuckling.
Cynthia
8.0/10
Good
Downtown is quite charming & well-to-do looking - lots of quaint shops & handsome historic houses. Short walk to the river & a short scenic walk there. Shopping areas on northern outskirts are a different story - lots of vacancies & decline.
John
8.0/10
Good
Chestertown is a nice town to raise a family. I would live in the outskirts but that is a personal preference. It is a nice college town.
"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."
"Solo dad on vacation, just looking for a good night's sleep on budget. Quality Inn came through for a very pleasant stay. Great A/C that was quiet, clean, spacious, actually had electrical outlets for my laptop and accessories.
Nice water pressure for shower, adjacent parking, first floor so no stairs. Friendly check in. Nearby amenities."
Can I book a refundable accommodation option in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates that you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a holiday rental instead of a hotel?
If you want a good alternative to a hotel, look over our selection of 25 holiday homes. In addition, you can choose from 9 apartments.
What will the weather in Chestertown be like during my visit?
July and August are typically the warmest months in Chestertown, when the average temperature is 23°C. January and February are the coldest months, when the average temperature is 4°C. August and July are the months with the most rain.
Why should I book my Chestertown hotel with Hotels.com?
There are lots of reasons to book your Chestertown trip with us: our free cancellations on selected hotels* gives you flexibility, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.
Find out more about Chestertown
Find out more about Chestertown
If you're looking for a place to get away, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodation options to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighbourhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.
