My wife and I traveled to Chestertown for a quiet celebration of our anniversary. We were quite pleased when we pulled up to the hotel. It was built in the early 1900's, and it still preserves that look. Another reviewer said it best when they said that it was a combination of a bed and breakfast, and a hotel. The check-in staff were friendly and accommodating. The room was small but cozy, and very clean.
The hotel had some nice looking food for dinner, but it was a little out of our price range. However, brunch the following morning was very tasty.
This is not a hotel for someone who wants everything to be perfectly new. This is also not a hotel for someone that the finest of every detail. But this is the perfect hotel for someone who likes to experience a bit of history in a great location of a small town.

The Imperial Hotel in Chestertown is a wonderful old jem! We stayed in the third floor suite which is very spacious, and has an old shabby chicness to it. The bedroom and bathroom are spacious and very comfortable. The time were spent in our suite was spent mostly on the private porch which runs all the way across the front of the hotel. The porch is a perfect place to sit and relax, read, enjoy a meal, watch the town come to life in the morning or roll up the sidewalks at night. We didn't eat at the hotel, but the staff we encountered were very helpful and pleasant. The art galleries, shops and eateries are all with in a short walk of the hotel. The river is a couple blocks away--kayaks, canoes and bicycles can be rented can be rented....a nice way t spend a hot August afternoon is on the river kayaking. The folks in this eastern shore town were very friendly.....the hotel, town and genral area is a treasure............we would stay again in a heartbeat!

We had lunch reservations for after my niece's Graduation, their was 9 of us in our party, the menu was very limited, so 3 of us got the "Cheeseburger" that was on the menu, we had our chose of what kind of cheese we wanted. When the two burgers arrived they had no cheese even though we specified the cheese we wanted, the third didn't arrive at all. When the waitress FINALLY showed up again, she took the burgers back and made them cheeseburgers as their menu stated. When everyone was almost done my burger came, the edges of the burger was rare but was ok to eat (I thought) when I got toward the middle is RAW, not rare, RAW not COOKED. Someone from our party got up to look for the waitress, he ended up finding the Manager who never came to the table to even apologize to all of us for the terrible service. To add to the story, The waitress only took 7 out of 9 drink orders, and 18% gratuities was automatically added to the bill. I can't remember eating somewhere where the service was that BAD.

My wife and I visited Chestertown, MD as a twenty-first anniversary trip. We had dinner and listened to live music up the street at a restaurant called "Andy's", and we spent the night at the Imperial Hotel. It was off season and bitterly cold, so there was not much activity in town. We were delighted with the accommodations, and very much liked the hotel. It fit perfectly with this historical town as an authentic small hotel with upscale detailing.

While you will find some scratched paint and a ding here or there, as you will in many commercial settings, I believe the management strives to ensure everything is kept in good condition, and more importantly that the visitor's needs are met. While it was 15 degrees outside our room was warm and I did not feel any drafts. We could control the heat for each room by window and floor units. In the summer it would be the same with A/C units.

I highly recommend the parlor suite, as we had ample space to stretch out, and there was a 3rd floor private veranda that would have been a relaxing place to watch the town happenings had we visited during a warmer season.

Having traveled to other large "renovated" spa hotels such as the Greenbriar in WV, Bedford Springs in PA, and Hotel Hershey in PA, I can say that this hotel was is like their small town cousin. It lacks the pool, the spa and shear facility size, but the feel is the same on an "inn" size scale.

If you want a local place to stay while visiting Chestertown, and you are not in need of the pool and spa treatment, and you are looking for value, then the parlor suite at the hotel is a good bet.

Additionally, we received vouchers for the continental breakfast in the dining room, or their value could be used toward our breakfast/ brunch meal. We choose a la carte items, and were very happy with our meal and desert. Once again the setting was upscale with table linens, china and silver settings.