Monthly Rentals in Chesapeake Bay

We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.

I had an incredible, incredible time at Jemma's place. She is a consummate hostess--she was responsive and welcoming even before I made the official decision to book (I sent her some queries before booking and she was so very helpful!) Once there, she was a lovely mix of warm and friendly, yet respectful of her guests' time and privacy. She even let me borrow her rain boots when I didn't pack any! I felt right at home at the house and on the island immediately... to the point that it was a little emotional leaving! I think it's worth noting (because I was concerned about this before my arrival myself, and some of the older reviews cast some doubt...): the internet at Jemma's is very fast and reliable! I depended on it for working remotely throughout my whole stay, and it never failed me throughout zoom meetings, webinar streams, etc. I would highly recommend this beautiful home to anyone!!

My wife and I needed a short getaway and Tia's place fit the bill. It is just as it looks in the photos - spotless and cozy. Tia is a great host and a nice person as well; she showed us her hens and chickens that are nearby and she is also a beekeeper. The house is comfortable and we felt right at home. It's only a short drive to many restaurants and antique shops; we will definitely be back when we need a little time away. Highly recommend.

We had an amazing stay here! Terri is so friendly, accommodating, and welcoming. This is one of the cleanest Airbnbs we have stayed at. It’s quiet, beautiful and had everything we needed. Highly recommend.