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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

Simply Bed and Bread

Show Prices
Certificate of Excellence
Enter dates for lowest prices
powered by PriceFinder
Prices from our online travel partners are not available
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In Check Out
Show Prices
View Map
Add a photo
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"moduleList":["handlers"],"divClasses":"prw_rup prw_ibex_photo_carousel","js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review
Turn Your Opinions into Points!
Turn your opinions into JPMiles
Turn your opinions into PAYBACK Points
*You can enroll in only one programme at a time to earn rewards for reviews.
JPMiles / Payback Arrow

186 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
There are newer reviews for Simply Bed and Bread
See the most recent reviews
Showing 186: English reviews
Alexandria, Virginia, United States
Reviewed 18 August 2012

Cheryl and David were absolutely delightful hosts -- they even took out their tandem and led us on a ride down to the river and through some lovely countryside. The room was lovely, very clean, the bed was firm (not worn out!!!) and the sheets downright cozy -- oh, and the food! Homemade snacks, cookies, and an absolutely heavenly breakfast....

Thank Theresa A
Southport, NC
Reviewed 11 August 2012

We thoroughly enjoyed our visit to Simply Bed & Bread. Hostess Cheryl is an outstanding chef and made the best breakfast we have had in a long time. Corn Omelet with Spicy Jack Cheese? Never heard of it but we will be on the lookout for it again. The cinnamon bun was too large to finish but the leftovers provided...

Thank kkarlSouthport_NC
Reviewed 11 August 2012

Full disclosure, I had never personally stayed at a B&B- Which has now turned out to be the worst thing ever because I am confident that no other B&B will measure up to Simply Bread and Bed. Sheryl and David are the most gracious hosts, one could not ask for more. It felt like we were staying with family (and...

Thank RonnieTy
Pittsburgh, Pennsylvania
Reviewed 29 July 2012

We were in Chestertown for a family reunion, and decided to stay at Simply Bed and Bread after reading their reviews on this site - once again, the reviews were very helpful, and we have to add our names to the long list of fans that Cheryl and Dave have. It was AWESOME! The rooms were fresh, clean, and very...

1Thank alexdavit3
Raleigh, North Carolina
Reviewed 28 July 2012

I stayed here for an interview with Washington College and from the minute I walked in, I felt like I was a Cheryl and David's long lost nephew. Being there for an interview, my experience probably differed from other guests' a bit. That said, the two of them could not have been more helpful in learning about the area from...

Thank Paul W
Oxford, Ohio
Reviewed 25 July 2012

Far and away the best band b I have stayed in, and I have stayed in many. The house is lovely and the hosts are utterly charming and clearly enjoy what they do. Cheryl is a terrific cook and I was lucky enough to test some of her delicious and unique home made ice cream. Furthermore, she sent me off...

1Thank Darcy D
Bellevue, Nebraska
Reviewed 22 July 2012

My husband and I visited Chestertown, Md., for a weekend away from the city and booked our stay at Simply Bed and Bread based on the many excellent reviews. And we were not disappointed! Upon booking the reservation, Cheryl called to see what our favorite breakfast foods were, favorite cookies to eat upon arrival, and other preferences. This hospitality extended...

3Thank navpa
Duncan, South Carolina
Reviewed 11 July 2012

My husband and I enjoyed a 3 night stay in this delightful bed and breakfast while visiting family in Maryland. Cheryl and David were so friendly and welcoming to their southern guests! Our room was lovely with a very comfortable king sized bed. There was so much attention to detail from the wonderful breakfast each morning to mints on our...

Thank Becky B
Roswell, New Mexico
Reviewed 28 June 2012

This bed and breakfast is just lovely! It's in a quiet residential neighborhood, yet a short walk will get you to the center of historic Chestertown and the Chester River. The owners are totally accommodating and friendly, calling before your stay to find out your favorite cookie so to have a fresh batch ready upon your arrival. Clean, neat, and...

Thank LokiRoswell
Reviewed 25 June 2012

Home, Mom, Chef Extrordinaré all rolled into one. The Inn was spotless. The hospitality was gracious. The setting was beautiful. We chose this B&B because of the proximity to Washington College. We traveled from VT to bring our 12 year old son to the CTY program summer camp at the college. This was the perfect blend of a peaceful retreat...

1Thank terischauer

20 photos of this hotel

Traveller photos: See what travellers like you saw

All Traveller Photos (17)
Room/Suite (4)
Dining (1)
Pool/Beach Area (1)
Other (11)

Management photos: Courtesy of the property manager

All Management Photos (3)
Room/Suite (1)
Other (2)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Chestertown
1.5 km away
Holiday Inn Express Hotel & Suites Chestertown
1.6 km away
Quality Suites
Quality Suites
#2 of 2 in Chestertown
110 reviews
31.3 km away
Hilton Garden Inn Kent Island
Show Prices
Show Prices
Show Prices
17.5 km away
Inn at Haven Harbour
Inn at Haven Harbour
#1 of 3 in Rock Hall
92 reviews
2.3 km away
Brampton Bed and Breakfast Inn
13.1 km away
Great Oak Manor
Great Oak Manor
#2 of 11 in Chestertown
332 reviews
Show Prices
Show Prices
Show Prices


  • Free High Speed Internet ( WiFi )
  • Free Parking
  • Breakfast included
  • Room Service
In your room
  • Air Conditioning
  • Refrigerator in room
  • Free Internet
  • Free High Speed Internet ( WiFi )
  • Free Parking
  • Breakfast included
  • 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 

Additional Information about Simply Bed and Bread

Address: 208 Mount Vernon Ave, Chestertown, MD 21620-1324
Region: United States > Maryland > Chestertown
Price Range: ₹ 6,479 - ₹ 9,097 (Based on Average Rates for a Standard Room)
Number of rooms: 2
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing

Questions & Answers

Here's what travellers have asked, with answers from Simply Bed and Bread staff and other travellers.
6 questions
Ask a question

See all questions (6)

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 travellers prefer

“Both rooms are amazing!”
 of 5 bubbles iambic1955, 21 Mar 2017 | Read review
“Emily's room is bigger than Erin's. Know that there is one shared bathroom for both rooms.”
 of 5 bubbles ARay_10, 23 Jan 2017 | Read review
“There are two rooms, one slightly larger than the other--both are fine.”
 of 5 bubbles AllanG21, 31 Dec 2016 | Read review
“They only rent out both rooms on the top floor if family is traveling together, otherwise, they rent the KING suite only.”
 of 5 bubbles songaid2, 29 Aug 2016 | Read review
“Two good sized rooms; shared bath.”
 of 5 bubbles joan262, 30 Jul 2016 | Read review
5 of 5