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Simply Bed and Bread

Traveller (17)
Room & Suite (5)
Dining (1)
Certificate of Excellence


Certificate of Excellence
Think home-y, not hotel.Think character, not cookie-cutter.Think individualized, not generic.Think fresh, not frou-frou.Think stocking feet, not stuffy.Think friendly, not formal.Private. Yet personal.2 cozy, spacious, allergy-friendly upstairs rooms in a 1947 Cape Cod on a quiet street 100 yards from Washington College. Close to the hospital, Heron Point, historic downtown and the waterfront.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Breakfast included
Non-smoking hotel
Room features
Air conditioning
Refrigerator in room
Non-smoking rooms
Good to know
Residential Neighbourhood
38Room tips
Traveller rating
  • 195
  • 10
  • 0
  • 0
  • 0
Time of year
Traveller type
  • Filter
  • English
Popular mentions
What a lovely b&b in Chestertown! Our hosts were friendly, thoughtful, and accommodating! Rooms were comfortable and quiet. Breakfast was sumptuous. Thanks, Cheryl and David for your eastern shore hospitality!
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Response from cherylhoopes, Owner at Simply Bed and Bread
Responded 23 Sep 2018
Thank you! We loved having you! ~ Cheryl & David
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I stayed here two nights and Cheryl was the best! The room was so comfortable and the breakfast was absolutely yummy. And she spent a lot of time answering my questions and explaining the city. I have stayed at a lot of B&Bs but this was most likely the best! Thank you, Cheryl
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Response from cherylhoopes, Owner at Simply Bed and Bread
Responded 24 Apr 2018
Oh my goodness, thank you!!!! It was wonderful having you! ~ Cheryl & David
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David and Cheryl are the most wonderful hosts. They are gifted with caring hearts and a joy in serving. From our first phone contact, when Cheryl asked what kind of cookies we liked, I knew these were special people. Their home is lovely, and our room was quiet, spotless,
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We stayed here one night. Our hosts were excellent and very accommodating even putting our bikes in their garage overnight.. Cheryl made as a wonderful breakfast - more than I could eat. Our room was spacious and there were lots of nice touches including a basket of snacks and
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Cheryl and David were terrific hosts. From the moment we stepped in the door, they were accommodating and helpful, while also letting us do our own thing. Cheryl cooked amazing meals and had extra treats waiting for us in the bedroom. They truly went above and beyond and
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Album Categories
All photosTravellerRoom & SuiteDining Pool & Beach
Emily Room
Photo provided by managementSimply Bed and Bread
the California King
Emily Room
Emily Room
Lovely room at Simply Bed & Bred
Mike and Madonna, Trip advisor sent me this comment, as my husband Brewster and I have stayed with Cheryl and David so many times, we consider them family! We are on our way to Simply Bed and Bread again tomorrow. It is because of their love and gracious hospitality that we were able to survive my mother in law's death this summer: Cheryl and David went out of their way to accommodate our whole family with hospital visits, lots of food, and more love and support that you'd ever believe! We are actually buying our own home in Chestertown because of these loving friends. Any questions you have about these awesome people and their lovely B and B, ask away ; I'm honored to answer! Pamela, aka ILoveItaly
0 votes
"There are two rooms. Both of them are beautiful."
"Both rooms are beautiful and quiet."
"Both rooms (only 2 available) located upstairs and share common bathroom"
"Only two rooms and both are GRAND!!"
"Both rooms are amazing!"
United StatesMarylandChestertown
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