Simply Bed & Bread

My stay with Cheryl and Dave was absolutely wonderful. I’m so glad I found their bed and breakfast while staying for a few days in Chestertown. I had a spacious, clean, beautiful room with chocolates, snacks and toiletries that made me feel comfortable and right at home. Cheryl is very kind and welcoming — she even asked my favorite kind of cookie and baked them on my arrival! Breakfasts were homemade and delicious. The quiche was fantastic! And it was nice to talk to Cheryl about the town. Book in advance because there are only two rooms (part of the charm and private feel of the stay!) I would absolutely recommend this b&b!

It’s all in the details, and this place does just that. My husband and I and our friends went last weekend, which was absolutely fabulous weather. The house is probably a 10 minute walk into the town and just up the street from Washington College. The rooms are charming, clean and comfortable with a basket of goodies. The two rooms share a bathroom. Cheryl and David are gracious and friendly innkeepers. Both are born/​bred in Chestertown so they are very knowledgeable about this charming town they love. We have stayed in many wonderful B&Bs, but I would rank the breakfast here right at the top. A delicious fresh fruit/​ice cream to start and I think there was another course before the eggs that escapes me at the moment. Omelets with veges and sausage and a wonderful eggplant side, with athick slice of farmer’s toasted bread. Of course, juice/​coffee/​tea. Additionally, there were these huge cinnamon buns to finish. This was a he-​man breakfast so we couldn’t eat the pastry. Instead, Cheryl kindly packed a cinnamon bun for each of us (one would have been enough for 4) with cookies.
Chestertown: very charming and authentic (no fast food or chain stores). It’s not too small (i.e., more than just «Main Street) or big; very walkable and it sits on the Chester River. A really lovely place to visit.

I was here with a friend about two years ago and it was both our first times staying at a local bed and breakfast. Let me tell you, Cheryl did NOT disappoint. There were cookies and coffee waiting for us as soon as we got in and the room was so cute and cozy. There are little snacks and treats around the room and we could sit at a small table overlooking the front yard while we munched on homemade chocolate mint cookies.
So many details go into your stay, such as Cheryl calling to ask what kind of food and treats we like, that it was like a home away from home. Dave and Cheryl are both so sweet and Cheryl is an amazing cook! I could seriously not even finish the breakfast there was so much food (seriously 4 courses). We were sad when our weekend was up but Cheryl sent us home with a goodie bag full of homemade cookies and bread. I would absolutely recommend this place to anyone staying in the area!

Last Summer, we were in Chestertown for a fairly large family reunion, and after checking out all of the hotel and motel options, decided to stay at Simply Bed and Bread after reading a bit more about the place on its website and online.
We simply have to add our names to the long list of fans that Cheryl and Dave have. Our stay here was AWESOME! The rooms were fresh, clean, and very comfortable, and the hospitality they showed went way above and beyond our expectations.
Cheryl is a Master in the kitchen! She prepared home-​baked cookies upon our arrival, and two incredible breakfasts to enjoy while we were there. Corn was in season, and her sweet corn and habanero ice cream is pretty much the best ice cream I’ve ever had. She also thrilled us with a watermelon gazpacho, which was refreshing and delicious.
The room rates are very reasonable, and this place is a wonderful value! We all enjoyed our conversations with Cheryl and Dave, and were really glad to add our pins onto their neat little map of the visitors the’ve had as guests.
We will definitely come back to historic Chestertown, and when we do, we will want to stay with the Hoopes’ — Thank you so much! Best B&B we have ever stayed at!

We traveled from New York for a wedding in Chestertown this fall, and were very happy with our stay at Simply Bed & Bread. Cheryl and David were welcoming and gracious hosts, the accommodations were very comfortable, and Cheryl’s cooking was delicious. Be sure to ask her for some of her fresh-​baked cookies as well.
Chestertown is a rather nice town, by the way. So, if you’re headed to town or taking a slow roadtrip to wherever, definitely consider stopping in here for the night.