Monthly Rentals in Chestertown

Lovely house in a beautiful and peaceful setting. Well equipped kitchen, bathroom and cozy, comfortable bedding and beds! I recommend Diana’s place for a peaceful and relaxing stay.

At the end of a quiet street, with its private rooftop deck overlooking the river (and beautiful sunrises), Franco’s place was the ideal choice for my four-day solo retreat. The apartment was comfortable, clean, and exactly as described, with nice touches like thick, fluffy bath towels; coffee, snacks, and cooking supplies; and plenty of closet space and hooks. Franco provided easy-to-follow directions and entry instructions. He and Daryl were perfect hosts—never intrusive but always available if needed. I highly recommend this listing!

The property was exactly as advertised. I thoroughly enjoyed my stay. It was very quiet which I liked very much. Roland was very helpful with check in and made our stay very nice.

My husband and I along with our dog Cash had a wonderful stay at Tom and Jen's place. It was very spacious and the view was spectacular. The fenced in yard was great for our dog who loved meeting and playing with their dog. Tom and Jen chatted with us when we first arrived and made us feel very welcome. The neighborhood was very peaceful and we really enjoyed taking our dog for walks during our visit. Everything was perfect! We would love to stay there again next time we're in Chestertown.