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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 865 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 bed and friendly staff
By Matt
Relative to a lot of Holiday Inn Expresses, this was a really nice property, with incredible waterside views. [Less]
Relaxing getaway
By Visiting from md
We decided to visit the Eastern Shore towns and decided to stay here based on the pictures. We are so glad we did. The rooms were big and clean. The beds were very comfortable. The views were [More] PRICELESS. We enjoyed the docks and chairs provided at the water. The breakfast was usual Holiday Inn Express Breakfast with wonderful staff. Will be going back :) [Less]
Kent Island Getaway
By Cherie
Very positive experience, we recommend this hotel and will stay there again. Very clean and comfortable. Convenient location to restaurants and fishing. Also close to the Tanger Outlet Mall. [Less]
Excellent Customer Service
By mdb1234
The entire staff was friendly and helpful! They were warm and welcoming from the beginning to the end of my stay. [Less]
Great stay, great price.
By traveler
Clean, comfortable, friendly, helpful staff, great breakfast. [Less]
IHG cHESTERTOWN mD
By Rick
Great HOTEL, NICE ROOMS AND GREAT STAFF, ease if parking, good food across the street [Less]

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