Flag House Inn Bed & Breakfast

26 Randall Street, Annapolis, Maryland 21401
Innkeeper(s): Charlotte & Bill Schmickle
  • Introduction

    Flag House Inn Bed & Breakfast dining room

    In historic Annapolis, Flag House Inn Bed & Breakfast has free off-street parking for your convenience, king-sized beds, private baths,  cable TV, AC, WiFi and only 1 block to City Dock & United States Naval Academy Gate 1.

    Flag House Inn Bed & Breakfast is a restored 1870 Victorian home which offers four guest rooms as well as a two-room suite.  We offer a non-smoking environment, with slumber sound machines in each room to provide a calming, soothing night. 

     From our front door you can walk to the Annapolis harbor for one of several boat rides, visit museums located in the area, peruse art galleries on Main Street, Maryland Avenue and West Street or just have fun shopping in the many unique shops about town.

    When you need a rest you can stop in at one of the many pubs and restaurants for some refreshment and relaxation. There is something for everyone!


    Flag House Inn Bed & Breakfast front of inn

    Park and walk to everything!

  • 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 Charlotte Schmickle for sharing her own secrets with BBOnline.com!
    Why do most travelers stay at your inn?

    Location, location, location! Free on site parking! We are located in the heart of the Historic District of Annapolis, MD which is the capital of MD but also home of the US Naval Academy as well as St. John’s College. Annapolis is also located on the Chesapeake Bay and was established about 1680 so we have many buildings from the 18th century still in existence and in use today.

    What are you best known for?  

    Probably best know for our Baked Blueberry French Toast and our Apple & Cranberry Compote – two of the favorites of our guests. Not to brag – but our reviews on line frequently have comments about how helpful we are, how our guests feel “at home” and how much people generally enjoy their stay with us.

    What makes your inn unique?

    What makes us unique comes in threes again. One is that ours is a paired townhouse which means the guests have one entrance and we have a separate front door entrance also. That way we have the charm of a B&B but all the privacy of much larger inn or hotel for our guests. A second and equally important uniqueness for folks who are interested in knowing anything about USNA is that we have a son who graduated from USNA and my husband, Bill, has been an adjunct professor there in years past. The third unique feature is for those interested in Historic Preservation and how it works in Annapolis. My husband, Bill, was chair of the Historic Preservation Commission here in Annapolis for over seven years and has published two books on the “Politics of Historic Preservation” in the past few years.

    What do you love most about your inn?

    What I love most about the inn is that we meet so many interesting people every day and have made many good friends over the 16 years we have been running the inn.

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

    One of the most beautiful and easily accessible Colonial cities in the US. 

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

    “I can’t wait to come back again.” (And, thankfully, we hear it often.)

    What’s the best kept secret about the area?

    The museum at USNA

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

    Spend on day at USNA (that may seem a lot but believe me there is lots to see and do there). A second day would be spent walking around town, visiting the historic homes and taking one or more boat rides, kayak adventure, bus tour of town, etc. A third day can be used for shopping, visiting Tawes Gardens or visiting Londontown. Then when leaving after the fourth night I would suggest places to visit on the way out of town (e.g. Chesapeake museum, a visit to Baltimore or into DC, a visit to Gettysburg, a visit to Fredericksburg or Quantico Marine Base, depending on which way one is heading when leaving Annapolis.)

    Is there anything within walking distance of your inn?

    Everything mentioned above (except Londontown) is within walking distance of our inn. That includes 20 – 30 restaurants, too.

    What is your favorite restaurant/food in the area?

    Annapolis is called Crabtown on the bay, so eating crab is a must when in the area. There are many many excellent restaurants in the area – some of my favorites to recommend to guests include: Galway Bay, Carroll’s Creek, O’Leary’s Seafood, McGarvey’s Pub, Osteria 177, Lewne's Steakhouse.

    Any good area guides/websites that travelers could reference?

    Our Convention and Visitor’s Bureau has a website at www.visitannapolis.org/ for some general information about sights to see in the area.

    How many rooms does your inn have?

    We have five rooms all with private bathrooms. We have one room with two twin beds, three rooms with king bed and a two-room suite that has one room with a king bed and second room of the suite has a twin bed.

    Do you accept pets?

    We do not accept pets in our B&B.


  • Rooms & Ameniies

    Flag House Inn Bed & Breakfast Two Room Suite

    The Flag House Difference:

    • Off-street parking on premises FREE for our guests
    • Private full bath within each room
    • King bed or twins in 4 guest rooms & a 2 room suite
    • Cable TV, free WiFi, soothing sound machine
    • Full hot breakfast in fine guest dining room.
    • Original naval and maritime art and antiques
    • Guest library with fireplace
    • Porch swings and teak benches
    • AC & ceiling fans in each room
    • Comfortable room seating & good lighting for reading
    • Restaurant menus, area guides, books & magazines
  • Area Attractions & Activities

    Flag House Inn Bed & Breakfast guy

    • Annapolis Summer Garden Theatre
    • Colonial Players Theater-in-Round
    • Jonas Green House
    • Navy Marine Corps Stadium
    • Water Taxi
    • Preble Hall Naval Museum
    • Sailing Hall of Fame
    • Annapolis Coach Tours
    • Chesapeake Marine Tours & Charters
    • Hammond Harwood House
    • Naval Academy Walking Tours
    • Naval Academy Visitors' Center
    • Paca House & Gardens
    • Governor's Mansion & Garden
    • Galleries & Shops
    • Chase Lloyd House
    • Shiplap House
    • Alex Haley Memorial
    • Maryland State House