Find Pet-friendly Hotels in Chestertown, MD from CA $87

"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

"We normally boat on the upper Chesapeake Bay and wanted to boat on different area of the bay. We rented a transient slip at the Tolchester Marina while staying at this bay house. We found the accommodations at this house to be wonderful. The house was clean and well equipped and plenty of space for my family of 7. Probably the most important thing to say - there was an unforeseen issue with the house water system. Jill was extremely concerned and very promptly had technicians coming to the...

"Place is FABULOUS!!! Fantastic location easy to walk around town. THANKS FOR EVERYTHING"

"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."

"Cute, clean, comfortable master bed, complimentary coffee"

"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."

"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"

"We greatly enjoyed our stay at the cottage. The location can’t be beat with coffee shops, bakeries, and restaurants all very close by. The three concerts we attended at Washington College and in Rock Hall were excellent. And “Buck a Shuck” oysters on Thursday at the Retriever Bar were a pleasant surprise."

"Was clean and good for the purpose of the trip"

"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"