The Guesthouse Bed and Breakfast

Loved our stay at The Guesthouse! The bed was insanely comfortable and the space had such a warm, cozy vibe. Everything was clean, well thought out, and felt very welcoming. Mitch and Miss Carol were so kind and accommodating. They really made us feel like family. Amazing service and attention to detail, and the food was incredible. Would absolutely stay here again!

I hosted a reading retreat for my wife's birthday at the Guesthouse. Mitch was the best host. I came to him with the dates, headcount, and a loose agenda, and he helped me pull off a perfect weekend. The space is perfect for unplugging and relaxing. We walked over to the Book Plate downtown to grab books, tried different foods around Chestertown, and slept HEAVY on the ridiculously comfortable beds. Much-needed time away. I should’ve taken more pictures of the breakfast! No misses at all. I can’t recommend this spot enough. I will be back.

The Guesthouse is such a lovely B and B in the charming town of Chestertown MD. The location was terrific- right in town and walkable to the college. We stayed there over Thanksgiving weekend. Mitch and his mother were incredibly accommodating. They even sent pictures of the stairway to ensure that my 87 year old mother could make it up the steps and were gracious when her grandchildren came calling. This old Victorian house has been lovingly restored. It manages to be quaint and comfortable, chic and historic, and welcoming yet elegant. The rooms and baths are gorgeous. And the breakfasts are spectacular. Home-made granola, farmers market yogurt and berries, freshly baked scones, cookies, crepes and omelets. This is a special place. We will be back next Thanksgiving--or sooner!

My mom and I stayed at this lovely, wonderful B&B last week, which is also owned by a mother and son team 😊. It exceeded our expectations in ways I could have not predicted: the house is exquisitely decorated, the home-made breakfast was just fresh and delicious (accompanied by perfect background music), and best of all, Carol and Mitchel were the perfect hosts, both kind and friendly. The house is also located within walking distance of the lovely town, with lots of restaurants and little stores to choose from. I cannot recommend The Guesthouse at Chestertown enough!

I had such a wonderful stay here! The interior design is absolutely beautiful and thoughtfully done, maintaining the historic charm while feeling cozy and inviting. It truly felt like being at home. Carol and Mitchel were hospitable and friendly, and the breakfast was delicious. I would definitely come back and highly recommend this place!