Simply Bed & Bread

208 Mt. Vernon Avenue, Chestertown, Maryland 21620
Innkeeper(s): Cheryl & David Hoopes
  • Introduction

    Simply Bed & Bread - Chestertown, Maryland

    You might notice the WAC Administration Building cupola out of the corner of your eye as you walk onto Simply Bed & Bread's brick path, since our house is just a stone's throw away from the college. Or it might be the inviting wicker chairs on the front porch that catch your eye as they seem to say, "Come on up and sit for a bit."

    But if you happen to come when there's a fresh batch of homemade cookies in the oven, you'll probably forget what's outside, respond to the cookies' invitation, and head straight to the dining room! (And the smell of chocolate raspberry coffee brewing won't hurt either!)

    We'd love to have you come and stay with us - especially if you're looking for location, location, location, that is, a location as far as convenience is concerned. We're not on the water, (although it's not far away), so that definition of "location" is not what we mean.

  • Insider's Info

    Travelers are always looking for memorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Cheryl and David Hoopes for sharing their own secrets with!
    Why do most travelers stay at your inn?

    B/c we're currently # 2 on Tripadvisor and b/c they may be visiting Washington College.

    What are you best known for? What makes your inn unique? What do you love most about your inn?

    a. A warm welcome, cookies, breakfast and the individual attention each guest receives (since we're only a 2 room inn)

    b. Simplicity and also allergy-friendly

    c. Our guests, the small size, trying new recipes, the flexibility in my personal life .

    If someone has never been to your city, what is the #1 reason to come visit?

    Small, historic waterfront town or to Washington College.

    What’s the best compliment you have ever received about the inn?

    I honestly can't remember. I did receive a tip a couple of years ago that was more than the amount paid for the stay. That was certainly cool! Quoting from the most recent note, though, (that I received yesterday), from Rachel, age 34, she wrote: "You are so dear to me. Thank you for such amazing kindness! xoxo" and on the flowers she put on our dining room table, she'd also written,"You two are as bright and cheerful as these flowers. Thanks for being wonderful friends!" 

    What’s the best kept secret about the area?

    That the area is here!

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    The self-guided walking tour, a cruise on the brand new packet ship docked 3/4 mile away from our front door, canoeing, cycling, the ipod walking tour (on a weekend), the theatre downtown, The Mainstay (a performance venue in Rock Hall, a nearby town), the Eastern Shore National Wildlife Refuge, the farmer's market (Saturdays only), plays, concerts, art exhibits (weekends), lectures (sometimes), shopping downtown in cool, specialty shops, visit the local ukulele club (Wed nights at 6 PM), special events, and one can always enjoy the quiet and peace of our tranquil street in our laidback town.

    Is there anything within walking distance of your inn?


    What is your favorite restaurant/food in the area?

    Brooks Tavern is the best, according to us. Lemon Leaf, Luisa's, Herb's Soup and Such, the Evergrain Bakery.

    Any good area guides/websites that travelers could reference?

    How many rooms does your inn have?


    Do you accept pets?

    No pets b/c of allergy restrictions - I believe the Brampton has a pet-friendly cottage, but I'm not certain. Rock Hall has a couple, I think.


  • About the Inn

    Simply Bed & Bread, front view

    Let us explain! Your college student might be on one of the Sho'Men teams and you might be in town to catch a game and decide that you're just too tired to return home afterwards. Check us out. Or maybe you're visiting the college with your prospective student. You can't get any closer to the college than Mount Vernon Ave! Park your car here, then just walk to campus!

    Perhaps, though, you have found yourself in Chestertown for a very different reason, like sitting by the bedside of a great aunt or a loved Grampy at either the hospital or Heron Point. We can work behind the scenes to make that easier for you, by picking up a sandwich for you or purchasing a take-out dinner from the newly renovated WC dining hall so that your unpredictable meal times could be accommodated. With only 2 rooms, we're small enough to practically make you feel like you're at your own house. In fact, that pretty much puts into a nutshell what we hope to do here at Simply Bed & Bread: to offer you not only convenience, but also the comfort, warmth and welcome of home.

    After leaving our front door, you'll be stepping onto the WC campus in just 2 minutes. We're not going to spoil all the surprises, you'll simply have to come and see! Stop in any time for a tour and a free cup of something hot - or something cold, if that's what the weather calls for. And who knows? You might just arrive when a fresh batch of yummy muffins or cookies is coming out of the over!

    Two bright, spacious, allergy-friendly rooms (One room has a Queen bed, and the other a California King) in a cozy 1947 Cape Cod in a great location.