We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
All 12 Chestertown B&Bs / inns

Simply Bed and Bread

Save Saved
You added Simply Bed and Bread to your Saves list
208 Mount Vernon Ave, Chestertown, MD
Hotel amenities
  • Overview
  • Reviews (122)
  • Photos (15)
  • Similar Hotels
  • Amenities
  • Q&A
  • Room tips (22)
  • Location
  • More
Simply Bed and Bread
Ranked #1 of 12 Chestertown B&B and Inns
Certificate of Excellence 2014
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In Check Out
Write a Review

122 people have reviewed this hotel

Traveler rating
    113
    9
    0
    0
    0
See reviews for
26
56
16
8
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 (22)
Date | Rating
  • English first
  • Any
English first
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

Was this review helpful? Yes
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.

Was this review helpful? Yes
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

Was this review helpful? Yes
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.

Was this review helpful? Yes
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."

Was this review helpful? Yes
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

Was this review helpful? Yes
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
Reviewer
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

Was this review helpful? Yes
Owners: What's your side of the story?
If you own or manage Simply Bed and Bread, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.
Manage your listing

Been to Simply Bed and Bread? Share your experiences!

Write a Review Add Photos & Videos

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

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (13)
Viewed
Dining (1)
Viewed
Room/suite (4)
Viewed
Pool/beach area (1)
Viewed
Other (7)

Management photos: Courtesy of the property manager

Viewed
All management photos (3)
Viewed
Room/suite (1)
Viewed
Other (2)
Hotels you might also like...
Check In Check Out
Price Your Stay
Select tags to find the hotel that's right for you.
All
hotels in Chestertown with
any amenities

Amenities

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 
Number of rooms
2

Questions & Answers

Questions? Get answers from Simply Bed and Bread staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travelers prefer