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Chestertown Hotels

Compare Hotels in Chestertown

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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 642 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

Hooray for Snoozapalooza
By rad74
From the moment we walked in until the moment we left we had humorous, friendly interactions with the staff. [Less]
Great Stay
By M2rock
Easy, convenient, extremely clean and great quality for the value. [Less]
Best staff ever!!!
By Dink69
We stay in Chestertown every year as we are Nascar fans and come for the fall Dover race. Beautiful town. This facility has it all--great staff, great breakfast, comfortable accomodations, just a [More] beautiful building. We plan to be in this hotel every year as long as possible to attend the races!! Many thanks to the staff for their caring about the guest's experience. Keep up the great work. It really shows!!! [Less]
Keep up the good work
By E Phil
The hotel is an excellent bargain. The water views are really nice. Everything was perfect except the maid came to early to clean the room. [Less]
hidden gem
By mango tango
this hotel is off the highway and adjacent to a yacht basin on the river. it is quite and close to two great seafood restaurants. rooms are clean and the staff friendly. overall a great stay. [Less]
Great night sleep
By Dragonfly210
Started each day fully refreshed from a very comfy bed and a great breakfast. Returned each evening to refreshments and relaxing on the deck overlooking the water. The staff suggested we utilize a [More] table in the meeting room to set up our evening snacks and refreshments and to make ourselves at home. They were very happy to suggest things to make our stay more convenient and enjoyable. When returning to this area, we will stay with them again, recommending others to do the same. [Less]

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To book more than 9 rooms for one stay or request a quote, please use our Easy Meetings  Link will open in new browser window. tool or call 1-800-MEETING (in United States, Mexico and Canada).