Monthly Rentals in Kennedyville

Ashli’s place was a great location for exploring Chestertown. It was an easy walk to downtown and the water. She was very responsive to all questions we had and very welcoming. The house was spotless and the beds were extremely comfortable!

A wonderful retreat on an unbelievable property. We were so surprised by the amazing views of the Chester River as well as the really well marked hiking trail. A bit out of downtown Chestertown, but totally worth the drive. Benjamin was a great communicator, and very flexible to meet our needs. ps. the cutest goats

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.

This was a perfect getaway! This place was so peaceful and refreshing! All the small little touches were very thoughtful. We will definitely be back!