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 exploring the galleries in Historical Society of Kent County Maryland during your travels in 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.
Wander cobblestone streets lined with 18th-century buildings, soaking in the colonial atmosphere of this historic Chesapeake Bay town. Sail the Chester River on a traditional skipjack, then browse antique shops and art galleries along High Street.
"Great location and staff! The hotel is nice - wish that they had a bar and restaurant on site but plenty of options within walking distance though. Nice view of the water and updated rooms."
"Only complaint, the blackout drapes were almost two feet too short. I had to barricade the windows with couch cushions to block the lights entering at the floor level up to two feet high. It would’ve been nice to have a light switch to turn off lights on the terrace (never found one).
That issue aside, bed comfort was decent with a variety of pillows. Bathroom was clean, room was comfy, spacious, had a great view (paid extra for it) and the hire is in a convenient location - within walking distance of some great seafood restaurants too. Hotel breakfast was what one might expect anywhere (meh) and it ended a little too early (9:30 am - should’ve ended at 10am)."
If you're looking for the flexibility to change your plans to Chestertown, most properties offer refundable* rates 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 vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 25 vacation homes. In addition, you can choose from 9 apartments.
What will the weather in Chestertown be like during my trip?
July and August are typically the warmest months in Chestertown when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. 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, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
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 accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods 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.
