Welcome to The Guesthouse

Each of our guestrooms is unique with its own personality and complete with everything you need to relax and unwind — premium toiletries, robes and linens, plush duvets for any season, and a small assortment of homemade treats. You won’t find a tv here, but each room has Wi-Fi access. Unfortunately, at this time we are unable to offer any ground floor accommodations, and we ask those who book to be aware of some of the unique features of this house, including the staircases and slanted ceilings.

~ Testimonials ~

“We recently had the pleasure of visiting Chestertown, Maryland for the very first time, and we are already planning our return. Our visit was initially prompted by the funeral of a dear friend, and we decided to arrive a day early to experience the town that meant so much to him. What we discovered far exceeded our expectations — most notably, our stay at The Guesthouse B&B and the warm, welcoming care we received from its proprietor, Mitchel.

From the very first moment of booking our reservation, Mitchel demonstrated a level of attentiveness and genuine hospitality that is rare to find these days. Upon arrival, we were instantly charmed by the house itself — its inviting layout, beautiful decor, and the truly magical “secret” garden tucked away in the back. But more than anything, it was Mitchel’s personal touch, passion, and attention to detail that made our stay so memorable.

Breakfast was nothing short of exceptional — delicious, beautifully prepared, and served with care. It was the perfect sendoff as we headed home. As former restaurant owners of over 20 years, we fully understand the challenges of providing consistent, top-tier service — and we can confidently say that Mitchel and his mother have created something truly special at The Guest House.

We would love to keep this little gem to ourselves, but we know that in order for wonderful small businesses like this one to thrive (and to be there the next time we visit!), we need to share our experience. If you’re planning a trip to the Eastern Shore, don’t miss the chance to stay at The Guesthouse — it is the epitome of heartfelt hospitality.” — June 2025

“My husband and I celebrated our wedding anniversary at The Guesthouse. We couldn’t have asked for a better weekend. From the moment we arrived until we left, our host, Mitchel, exceeded our expectations! He was attentive to our needs and gave us time to enjoy the beautiful architecture and design of the B&B. Mitchel recommended an exceptional fine dining restaurant in the neighborhood to commemorate our special occasion. His thoughtfulness will always be appreciated! The following day, we enjoyed a delicious home-cooked breakfast and a trip to the farmer’s market. I highly recommend The Guesthouse for a special occasion or weekend getaway. It is a fantastic experience of great hospitality, relaxation, and renewal!” — April 2025

“If you are anywhere in or around Chestertown, Md and need overnight accommodations, you must book a room at the newly remodeled Bed and Breakfast, The Guesthouse, on Washington Ave. An absolute beautiful redo from top to bottom!  The bedroom we stayed in had its own private bathroom that was quaint and had the comfiest bed.  As early risers, we were greeted in the morning with a cup of hot coffee on the side porch while we read and waited for breakfast to be served.  Each room has its own personal touches and two of the rooms have their own private clawfoot tub to soak in! The owners, Carol and Mitchel, mother and son, will be happy to recommend the perfect place for dinner that’s just a quick walk around the corner! Check it out, it won’t disappoint!” –April 2025