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Chestertown Hotels

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Finding a hotel is easy. Your destination can be:

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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 433 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.

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Latest Chestertown Hotel Reviews

Average Rating for Chestertown Hotel
(4.6 / 5) of 433 reviews
By whitetail1
My visit purpose was rest, comfort, sleep, breakfast,exit. All was provided as hoped or exceeded my expectations. [Less]
Location Location Location
By Laxdad3
This Hotel is very convenient for anyone visiting the Eastern shore, Annapolis, or Washington college. Staff is friendly and helpful and the facilities are clean and bright. [Less]
chestertown holiday inn, maryland's eastern shore
By Mister Baltimore
exactly what we wanted for what we needed. clean rooms as always, pleasant staff, good pancakes in the morning and great sausage gravy for the biscuits. fresh coffee was ready in the great room by 4 [More] a.m., which we were appreciative of. [Less]
very friendly staff
By ed0100
The staff here are all very friendly and treat us like family. Room and grounds are very well maintained. Always enjoy our stay. [Less]
Comfortable bed, great setting and service
By Joanie32
Great property. Always a comfortable bed with friendly helpful staff. Good value in this location! [Less]
Great service
By Carole1302
Wonderful people at this Holiday Inn The service was great and I had a wonderful time at my retreat [Less]

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