Monthly Rentals in Chesapeake Bay

We can’t say enough about the warm and hospitality of our hosts! Not a single detail was overlooked. The area was private, but what was overwhelming to us was the abundance of natural beauty everywhere! We had a lake on one side of the driveway and the creek on the other! The cottage was indeed very romantic, and we cannot wait to come back. We love that they had kayaks and we had a great time paddling the creek. There were some great restaurants in nearby towns, but if you didn’t want to go that far, a grocery store and Walmart were a few miles away.

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.

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!!

Very quaint, peacful and relaxing. Strange lay out, floor plan but it works. Good location. Quiet pretty, historic town.