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
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

124 reviews from our community

Traveler rating
See reviews for
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 (23)
Date | Rating
  • English first
  • Any
English first
  • All months
  • Mar-May only
  • Jun-Aug only
  • Sep-Nov only
  • Dec-Feb only
All months
1 review
5 of 5 stars Reviewed 3 days ago NEW

We recently stayed here when attending a family wedding. The hosts were wonderful. The rooms were nice with comfy beds. They met my need for a gluten free diet for breakfast. The breakfast included fruit, yogurt and a warm entree that was tasty. Cheryl asked us about our likes and dislikes when we booked our rooms and made meals that... More

Was this review helpful? Yes
New Jersey
11 reviews 11 reviews
5 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 2 weeks ago

Four of us met at this B&B for an overnight and we had the best time. The host and hostess go out of their way to make you feel at home. Cheryl made special food for our GF friend and also a birthday cake served with ice cream which we all enjoyed. We shared wine on the porch and walked... More

Was this review helpful? Yes
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
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

Was this review helpful? Yes 1
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
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): $
Number of rooms: 2

15 photos of this hotel

Traveler photos: See what travelers like you saw

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

Management photos: Courtesy of the property manager

All management photos (3)
Room/suite (1)
Other (2)
Hotels you might also like...
Check In Check Out
Price Your Stay