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All 12 Chestertown B&Bs / inns

Simply Bed and Bread

208 Mount Vernon Ave, Chestertown, MD
Hotel amenities
Simply Bed and Bread
Ranked #1 of 12 Chestertown B&B and Inns
Certificate of Excellence 2013
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116 people have reviewed this hotel

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (21)
Date | Rating
  • English first
  • Any
English first
Forest Hill, Maryland
1 review
5 of 5 stars Reviewed March 9, 2014 via mobile

A surprise birthday gift from our children turned into a home away from home. Cheryl had a cake ready for me when we entered their home and her hospitality went far beyond any other bed and breakfast we experienced. The breakfast was enormous and so delicious. If you ever decide to explore Chestertown, this is the place to stay. They... More

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Silver Spring, Maryland
Senior Contributor
23 reviews 23 reviews
5 hotel reviews
14 helpful votes 14 helpful votes
5 of 5 stars Reviewed February 8, 2014 via mobile

There is a hotel chain that touts " no surprises". I look for them at Bed and Breakfasts and Simply Bed and Bread delightfully delivered. The room was excellent with added touches like Itty bitty type book lights. 2 pleasant quiet might sleeps were enhanced by the Innkeeper/chef's tailored delicious and ample day starters combined with enjoyable and informative tales... More

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Madison, Wisconsin
1 review
5 of 5 stars Reviewed February 3, 2014

Can't imagine more warm, welcoming, caring hosts! From our first e-mail inquiry to our final good bye, Cheryl and David Hoopes anticipated and met our needs far beyond our expectations. Our trip centered on exploring the Chestertown area. Within days of our booking, we received a packet of materials "to study" before our arrival. Life-long residents of the area, Cheryl... More

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Elkridge, Maryland
4 reviews 4 reviews
5 of 5 stars Reviewed December 10, 2013

Very great place to stay for a laid back weekend. We planned to go to Chestertown just to have a bed and breakfast experience. This was our first B&B and we loved every part of it. Cheryl and Dave are so kind and make a great hosts.As soon as we walked in, we really had a great feeling, like going... More

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Birmingham, UK
Senior Contributor
38 reviews 38 reviews
16 hotel reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed November 6, 2013

From the moment we enquired Cheryl and David couldn't have been better hosts. It began with cookie requests and tips about the local area via email. And then the stay! We were visiting our son, studying at Washington college for a year and stayed 11 nights, the most we have stayed in one place on a holiday! We had planned... More

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Washington DC, District of Columbia
4 reviews 4 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 13, 2013

I've traveled around the world twice for a year each time and since then have traveled extensively, but I have never experienced as wonderful, warm and welcoming B&B like Simply Bed and Bread. Before I get to the important part, let me just reassure you that the rooms are lovely, decorated with quilts, handcrafts, antiques, super comfortable bed, plush towels... More

Was this review helpful? Yes 1
Boston, MA
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 18, 2013

I traveled down to Chestertown for the Maryland Swim for Life. I knew this B&B would be awesome right from my first phone conversation. Cheryl asked what my meal preferences were so that my swim would be just perfect. She also asked what my favorite type of cookie was so that when I arrived she would have baked some for... More

Was this review helpful? Yes 1
Greensboro, NC
1 review
5 of 5 stars Reviewed August 11, 2013

We stayed at Simply Bed and Bread while visiting Chestertown for a family wedding. We wanted somewhere different to stay rather than the typical hotel and we definitely found it (and more!) here. It felt like going home to visit dear family and friends. Cheryl and David met all our needs and then some. They greeted us with cookies and... More

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Keller, Texas
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed July 30, 2013

My family and I stayed at Simply Bed and Bread while visiting Washington College. I was overwhelmed by the great experience my family and I had while staying with Cheryl & David Hoopes. Cheryl is the nicest woman you could ever hope to meet and she truly cares about everyone who steps through her door. Describing her is hard, because... More

Was this review helpful? Yes 1
Arlington, Virginia, United States
2 reviews
5 of 5 stars Reviewed July 10, 2013

My fiance and I recently stayed for a weekend and had a wonderful experience. We are getting married in a few weeks and wanted a weekend to de-stress. Cheryl and David greeted us with cookies and ice cream as well as a goodie basket in our room. They were extremely polite and gracious hosts and were always looking to offer... More

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Additional Information about Simply Bed and Bread

Address: 208 Mount Vernon Ave, Chestertown, MD
Location: United States > Maryland > Chestertown
Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Room Service
Hotel Style:
Ranked #1 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $
Official Description (provided by the hotel):
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. ... more   less 

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