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Chestertown Hotels

Compare Hotels in Chestertown

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Destination
Finding a hotel is easy. Your destination can be:

  • a city (San Francisco)
  • an address (123 Main St., Springfield, IL)
  • an airport (LAX)
  • a point of interest (Fenway Park)
  • Zip Code (30308)

Featured Chestertown Hotels

Whether it's your first visit or Chestertown is a favorite travel destination, get ready to explore all that Chestertown has to offer and find the perfect temporary home base with help from IHG. Our easy-to-navigate website allows you to compare the best hotels in Chestertown by reading through our honest 715 reviews from verified hotel guests. When you book your room with IHG, you're assured a great deal and lowest rate with our Best Price Guarantee. We boast 2 hotels in Chestertown, MD, all with a distinctive flair and a variety of amenities, and you can conveniently narrow down your choices and book your room directly with us.

No matter if you're travelling to Chestertown to attend a conference, unwind on vacation, or enjoy a romantic weekend getaway, we have you covered. And if your travels take you to another part of the world, you'll find an IHG accommodation that meets your needs. From hotels in the heart of it all to luxury accommodations off the beaten path, IHG offers great hotel deals in Chestertown and throughout the world.

Enter your travel dates to view the best offers on hotel rooms, and use our advanced search features to find the hotels with the amenities you desire. When you stay as an IHG Rewards Club member, you also enjoy free in-hotel Internet access. Some of our hotels boast indoor swimming pools, while others offer hot breakfast, in-room kitchens, and spa services. We make it easy to book the perfect hotel for your trip.

Latest Chestertown Hotel Reviews


Beautiful view and great service
By Lenny
We loved the property with its beautiful water views. The front desk staff was warm and welcoming. We forgot something from home and they had a supply at the front desk. We just called and problem [More] solved. It was very affordable. It met all of our expectations, it was a great place to stay. [Less]
Mike
By Mike
Very much liked the stay! Only disappointment was that HIKI has no fitness/exercise room, but I was told that they had an arrangement with an off-site gym at $5/day. [Less]
Great Stay
By MCHarkins
Location is perfect for a nice weekend away. Went to Jetty for lunch and Annies for the Super Bowl. Great Super Bowl Buffet! [Less]
Excellent place to stay
By IHEmember21
I've stayed at the Holiday Inn Express in Chestertown on several occasions. They always offer excellent service and clean, comfortable rooms. I would certainly stay here again the next time I have to [More] travel to the area. [Less]
Good service
By Mr Mike
The front desk employees were very friendly and helpful. Had great recommendations for dinner [Less]
Great stay for a college visit
By Dawn B.
We visited for an Open House at WAC. The hotel was so close to the college and was very convenient. We were happy with the cleanliness and comfort of the room and enjoyed our stay. [Less]

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