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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 749 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


Comfortable clean pet friendly
By Restoner
Very comfortable and clean. We brought our 60 pound dog who was comfortable and happy. Food service for breakfast was rated slightly lower because there aren't enough tables to eat at and staff let [More] items run out and clients had to wait for new food items to be prepared. [Less]
Chestertown Holiday Inn Express Experience
By 16Cheryl
This hotel is clean, comfortable with an excellent staff. From the front desk to the housekeepers to the maintenance staff, everyone makes us feel welcome! the breakfast is great and offers a good [More] variety. The great room is always clean and we have used it for family game night or just picking up a pizza for a late snack! We will continue to use this hotel for the coming years! [Less]
Great service
By TomM
Wonderful check-in staff. Great breakfast.. We will make HI our default choice. [Less]
Comfortable beds nice breakfast
By CaptaininFl
Ask for water views when making your reservation . Very busy and noisy 50 but you cannot hear it from the hotel on the waterview side. We saw deer in the evening on the grounds of the hotel . Lots [More] of birds on the water side and even saw a family of river otters. [Less]
excellent p;roperty
By Freedom 42
Boaters paradise, lots of marina's, bars and resturants in walking distance. Very Clean and modern rooms. [Less]
My overnight stay.
By Harley Deluxe
We went on a short motorcycle adventure. I chose this location because of the variety of dining and scenic options. We were completely satisfied with our overall stay !! Thank you Holiday Inn. [More] Express!! See you soon! [Less]

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