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All 12 Chestertown B&Bs / inns

Simply Bed and Bread

208 Mount Vernon Ave, Chestertown, MD
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  • Reviews (121)
  • Photos (15)
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Simply Bed and Bread
Ranked #1 of 12 Chestertown B&B and Inns
Certificate of Excellence 2014
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121 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
Dublin, Ohio
1 review
5 of 5 stars Reviewed 2 days ago NEW

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 1 week ago

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 4 weeks ago 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
23 reviews 23 reviews
5 hotel reviews
15 helpful votes 15 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

Was this review helpful? Yes 1
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

Was this review helpful? Yes 1
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
12 helpful votes 12 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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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): $

15 photos of this hotel

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Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Room Service
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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