Find beach hotels in Chestertown, MD from CA $151

"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"

"This is a great place to relax. The house had everything we needed and was very comfortable."

"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 ."

"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."

"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!"

"This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the...

"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "