Simply Bed & Bread

208 Mt Vernon Ave , Chestertown, MD 21620 USA (Show map)


Ahh....the aromas of fresh bread baking, chocolate chip cookies just out of the oven, "scrubbed-squeaky clean" and sheets hung out on the clothesline...Simple. Subtle. The amenities of home. Quiet. 100 yards from Washington College, 10 minute stroll to historic downtown, 15 to the Chester River. Check Tripadvisor Reviews.



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  • Guest room4.7
  • Service5
  • Value4.8
  • Cleanliness4.9
  • Onsite Dining4.9

Curt and Sophia

5 on February 16, 2016

We had a wonderful time...Thank you so much

Simply Sweet

5 on November 10, 2015

Lovely, charming B&B, right in the heart of Chestertown. Well-appointed, cozy room, comfy bedding, unexpected goodies surprise you everywhere. Cheryl and David are splendid hosts, and Cheryl's home-cooking and baking skills are phenomenal. You will not leave hungry. I look forward to many fabulous future visits!

Simply Bed & Bread-Simply Wonderful!

5 on October 05, 2015

We could not get hotel accommodations and were concerned about trying a bed and breakfast, but what a delightful surprise! Spotless, comfortable rooms and thoughtful, generous and welcoming host and hostess made this a terrific place to stay. My daughter was playing with National Music Festival and Cheryl invited her to share the delicious, abundant breakfasts with us. Everything was so good, fresh and homemade by Cheryl, who besides being delightful company, is an excellent cook! Her presentation is beautiful as well. David was great with directions, and suggestions of places to see. We had fresh cookies waiting for us when we arrived and were given a generous bag of cookies for ourselves and our daughter for the trip home. They are a great team and do this right!

Our first B&B experience, excellent choice

4.8 on January 19, 2015

You know how some really rich people, instead of living in a big house that they have to maintain and keep up, choose to live in a hotel so that everything is constantly being refreshed for them and they don't have to do anything for themselves? This was like the perfect version of that. Great bedrooms, with the comfiest bed I've slept in. The best hosts who made us an endless breakfast. The location was a perfect getaway and/or jumping-off point to explore quaint Chestertown. For what we did (couple's weekend) it could not have been done anywhere better than this.

What a lovely weekend!

4.8 on January 18, 2015

First experience at a B&B and we couldn't have been more pleased! So welcoming, knowledgable, and friendly. Felt comfortable right away. Cookies (hello! so good.), tea, and Chestertown low down when we arrived. Great restaurant recommendations. Town was around the corner and Washington College literally down the street. Room with a very comfortable bed and anything you could imagine needing. And of course the most terrific breakfast in the morning! Better than I was expecting. Such a friendly couple run Simply Bed and Bread. We even chatted almost 3 hours of the morning away! Cozy small town that I would have never guessed to visit. Even less than an hour and half from Baltimore, but a great escape.

Perfect Weekend Get-away!

3.8 on December 15, 2014

Our weekend engagement weekend was perfect! The owner helped me with all my arrangements for my engagement proposal. Awesome! We felt like locals the whole time we were there.

Home Away From Home

5 on September 04, 2014

Out of all the Bed and Breakfast's in MD, this was definitely the best one! The food was delicious and catered to meet your needs! The rooms were spotlessly clean! Dave and Cheryl made us feel so comfortable and were amazing hosts. They also were informative about what was happening in the area! We highly recommend "Simply Bed and Bread" and would not hesitate to stay there again and again!

Far more than Simply...

4.8 on February 03, 2014

From my initial contact to our good bye, Simply Bed and Bread far exceeded our expectations. Our goal to explore the Chestertown area prompted Cheryl to send us a packet of reading materials to "study" before our arrival. She and her husband David, life-long residents of the area provided us with local knowledge and their "favorites." Our afternoon "tea time" was filled with wonderful homemade crackers, cheese and fruit -- a more than satisfactory substitute for Cheryl's usual delicious cookies. We appreciated the option of a non-sweet alternative. Breakfasts were a perfect combination of healthy, sweet and savory treats -- steel-cut oatmeal, fresh fruit, quiche, homemade bread -- a more than ample meal to sustain us through a day of experiencing the charm and history of the area. A comfy and luxurious King bed and a "butler's pantry" filled with whatever was forgotten provided a wonderful end to the day. But what was by far the most important quality of Simply Bed and Bread was the gracious welcoming atmosphere that Cheryl and David create. They share their home and their town but they share themselves. They answered our questions, gave a "virtual tour" of their community with stories of their lives and "happenings" in Chestertown. Warm and friendly are words that just touch the surface of the Simply Bed and Bread experience.

A very Nice bed, when you need to sleep

5 on December 30, 2013

we say thank you for 4 wonderful days at Cheryl and David in simply bed and bread. we got really good treatment, wonderful breakfast and good advice about the area. highly recommended place to stay. Emily, Kristine and Lotte Vitoft

My home away from home

5 on February 09, 2013

My wife and I have come here many times a year over the past several years. We live in New Hampshire, but travel to Chestertown to see my mother at Heron Point. Simply Bed and Bread has been more than a comfortable room and wonderful breakfast. It is a place where we can not only unwind after an emotional visit, but a place where we feel uplifted and refreshed. Staying here is something we genuinely look forward to. David and Cheryl have become friends who have gone the extra mile in helping us in more ways than I could ever recount. This is a very special place, and the cookies are great too.

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Location Type

Small town


Baltimore, MD (BWI-Baltimore Washington) 75 miles

Directions to property:

See website.

Area Attractions

Antique Shopping, Art Galleries, Concert venue, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, Nature area, Performing Theater, Picnic area, Religious Services, River, Vineyard, Winery

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Inn Details

On-site amenities

BBQ grill, Computer, Copier, Fax Machine, Secretarial services, Washer/dryer

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Board games, CD player, Coffee/Tea facilities, Desk, Fridge, Hairdryer, Internet Service, Ironing Board, Library, Satellite/Cable TV, TV, Wi-Fi, Wired internet

On-site activities

Bicycle rental, Bicycle riding trails, Bird watching, Boating, Canoeing, Fishing, Hiking trails, Horseback riding, Hunting, Kayaking, Only canoe & tandem bicycle on premises., Activities are available in our area., Sailing, Shopping, Sight-seeing, Swimming, Swimming pool, Water sports

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  • Check In:: 3 P.M.
  • Check Out:: 11 A.M.
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Alcohol Provided No
  • Suitable For Children: Yes Prospective guest "interview" determines compatibility.
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Minimum Stay: Chestertown's busiest weekends only.
  • Accepted payments AMEX, VISA, Discover, Mastercard, Diners club, Travelers checks, Cash
  • Deposit Amount Required: Credit card guarantee.
  • Cancellations: One week.
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Cheryl Hoopes

Languages spoken


About the innkeepers

Walking, reading, quilting, Grammy-stuff, Ukraine, new recipes, and of course, PEOPLE!!

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  • Time Served: At guests' requests
  • Serving Location: Coffee on front porch, Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian

Signature Dish

Homemade cinnamon buns --
Vanilla buttercream icing dripping off warm, soft, homemade, melt-in-your-mouth buns swirled with cinnamon.

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