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Simply Bed and Bread

208 Mount Vernon Ave, Chestertown, MD
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149 Reviews from our TripAdvisor 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
Traveler tips help you choose the right room.   Room tips (28)
Date | Rating
  • English first
  • Any
English first
  • All months
    (149)
  • Mar-May only
    (40)
  • Jun-Aug only
    (55)
  • Sep-Nov only
    (30)
  • Dec-Feb only
    (24)
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2 reviews
5 of 5 stars Reviewed 5 days ago NEW

We were in Chestertown for a wedding and made our reservations far in advance. The loveliness of the wedding was enhanced by the care and attention we received from Cheryl and David. The breakfasts were delicious and the mealtime conversations made our three days a happy memory. Straight-from-the-farm and made-from-scratch are not my everyday fare; thus Simply Bed & Breakfast... More 

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2 reviews
5 of 5 stars Reviewed 2 weeks ago

Cheryl is a wonderful, attentive, friendly hostess and (an award-winning) cookie baker! Anything you might need is at Simply Bed and Bread, with many unexpected extras and the BEST breakfast. Location is in a quiet residential neighborhood, just a short walk to Washington College or a stroll to downtown Chestertown. Chestertown is a real gem, with architecture from the 1700's... More 

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Crown Point, IN
Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed 2 weeks ago

My friend and I rented the two bedrooms here and had a lovely stay. We were visiting another friend nearby. Simply Bed and Bread's location is ideal - within easy walking distance to the center of town and Washington College. At the same time, it is quiet, comfortable, and owners Cheryl and David made us feel very spoiled with cookies,... More 

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Jacksonville, United States
Level Contributor
3 reviews
5 of 5 stars Reviewed 4 weeks ago

I've never stayed any place that is more focused on the wants, needs, and comforts of the guests. I do plan to return and will wholeheartedly recommend Simply Bed and Bread to anyone traveling near Maryland. It's just a short walk from colonial downtown Chestertown and the river, and an even shorter walk to Washington College. By the way, the... More 

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Towson, Maryland
Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed 4 weeks ago

We went to Simply Bed and Bread for an anniversary get away in April (okay, I know I'm late with my review). It was just perfect. The inn keepers are so sweet and made us feel like family with their hospitality. There was a red velvet cake waiting for us when we arrived (just like our wedding cake). When we... More 

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Melbourne, Australia
Level Contributor
5 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed July 12, 2015

This was a very special visit as I had come from Australia and only had two days to catch up with my daughter who is working just outside of Chestertown. Simply Bed and Bread was the best place for peace & quiet when you need it, and also for family warmth from hosts, Cheryl and Dave. They were considerate of... More 

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herndon,va
Level Contributor
8 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed July 9, 2015

I was looking to spend a night in Chestertown, but not stay at a hotel. Found Simply Bed and Bread for the right price online and stayed a night. The owner wanted to know what type of cookies I liked prior to arrival, and sure enough Cheryl had them for me on arrival. Room had a nice size TV, something... More 

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williamsburg
Level Contributor
5 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed July 1, 2015

This an absolutely delighteful guest house on a lovely street. The hosts, Cheryl and Dave were the most delightful hosts imaginable. I stayed in the smaller of the two bedrooms which was actually quite large and very comfortable. A basket of snacks was in the room along with a guest info book informing you where everything is such as the... More 

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Philadelphia, PA
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 3, 2015

When I first called Simply Bed & Bread, I said that my husband and I were looking for a "home away from home" for our frequent trips to Chestertown. We truly found it, times ten. David and Cheryl Hoopes are the B&B B hosts of your dreams. When we arrived yesterday, we weren't sure if we would stay one or... More 

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Carbondale, Illinois
1 review
5 of 5 stars Reviewed May 27, 2015

This was our second stay and it was as enjoyable as our first. The room was quiet and the bed comfortable. Breakfast was ample and delicious. David and Cheryl are very welcoming. They provide everything you might need or might have forgotten to pack. They also told us about the history of the area, being that we were visiting just... More 

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Amenities