Photo by Assya A

Hotels in Chestertown

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

Tonight
11 Feb - 12 Feb
Tomorrow
12 Feb - 13 Feb
This weekend
14 Feb - 16 Feb
Next weekend
21 Feb - 23 Feb

Where to stay in Chestertown?

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (331)
The price is €73
includes taxes & fees
24 Feb - 25 Feb
Red Roof Inn & Suites Chestertown
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.

Top landmarks in Chestertown

Washington College

If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.

See properties in Washington College
Washington College

Learn more about Chestertown

Notable for its university life, Chestertown features attractions such as Rolphs Wharf Marina and Historical Society of Kent County Maryland. The city has something for everyone including sights like Garfield Center for the Arts at the Prince Theater and Wilmer Park within a small-town setting.

See all hotels in Chestertown
Photo by Assya A
Open Photo by Assya A

Frequently asked questions

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 27 holiday homes. In addition, you can choose from 7 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.