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All 12 Chestertown B&Bs / inns

Simply Bed and Bread

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208 Mount Vernon Ave, Chestertown, MD
Hotel amenities
Simply Bed and Bread
Ranked #1 of 12 Chestertown B&B and Inns
Certificate of Excellence 2014
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122 reviews from our community

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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
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Gurabo, Puerto Rico
2 reviews
5 of 5 stars Reviewed July 26, 2014

My daughter was attending CTY Summer Camp at Washington College and we stayed here. Breakfast was so copious and delicious (ask for the cinnamon roll). The Emily room is so beautiful and charming. David and Cheryl was super nice with us. They made us (handwriting) a "Things to do list" in Chestertown. My husband was expended hours talking with Cheryl... More

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Dublin, Ohio
1 review
5 of 5 stars Reviewed July 23, 2014

My son was attending a camp at the local university and he and I stayed here. What a find. Cheryl and Dave couldn't be nicer people and completely took care of my son and I. Chestertown is a nice town to visit and Cheryl is very helpful in making the most of your stay. Thank you for a great visit.

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Baltimore, Maryland
1 review
5 of 5 stars Reviewed July 15, 2014

My husband and I stayed at Simply Bed and Bread for a weekend getaway. What an incredible experience! Cheryl and David are warm and friendly, and offered tips for the area. We were greeted with the best cookies I've ever had, and had two phenomenal breakfasts (home made ice cream with breakfast? yes please!). My husband was quite impressed with... More

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Baltimore, Maryland
1 review
5 of 5 stars Reviewed June 22, 2014 via mobile

Cozy Cape Cod on a quiet street. It is well appointed and immaculate. Breakfast was copious and unbelievably delicious. Owner even helped me locate bike shorts since I left mine home! I highly recommend this B & B.

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1 review
5 of 5 stars Reviewed June 2, 2014

Two comfy rooms at the top of the stairs with a shared bathroom. A two minute walk to Washington College, ten minutes to downtown Chestertown. Two friendly innkeepers. Delicious breakfasts served on *our* schedule. Our family would return and recommend. Our 13 YO son after this, his first stay at a B&B says, "I like B&Bs better than hotels."

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Middlesex, New Jersey
2 reviews
5 of 5 stars Reviewed May 18, 2014

We found Simply Bed & Bread when our son was a freshman at Washington College. Cheryl and David's hospitality, warmth and dedication to ensuring their guests' every possible need kept us returning for four years. The attention to detail and the amazing breakfasts are unrivaled no matter where we have traveled. The goodie bags to take home are a plus!... More

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Forest Hill, Maryland
1 review
1 helpful vote 1 helpful vote
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

Was this review helpful? Yes 1
Silver Spring, Maryland
Senior Contributor
24 reviews 24 reviews
6 hotel reviews
16 helpful votes 16 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
1 helpful vote 1 helpful vote
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
5 reviews 5 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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Additional Information about Simply Bed and Bread

Address: 208 Mount Vernon Ave, Chestertown, MD
Location: United States > Maryland > Chestertown
Price Range (Based on Average Rates): $
Number of rooms: 2

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