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.
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.
"Nice size room (#3329), clean, comfortable and quiet - everything we ask for in a hotel room! Front office staffer and valet team friendly and helpful. Hotel itself is an easy walk to all the shopping and restaurants. Would definitely stay here again."
The Inn at Henderson's Wharf, Ascend Hotel Collection
10/10 Excellent
"I loved room 121. It was a beautiful architecture and view. Very quiet and comfortable. The hosts were super friendly, offered us a check in drink, but I was almost late for my BYOB Urban Pirate cruise, so I had to decline. There is a bakery right around the corner, and lots of great food and shopping to walk to. I was there to enjoy the old town walks and shops and I sure did!"
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.
