Flag House Inn

Large porch with wooden steps leading to bed and breakfast

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About Our Historic Accommodations in Downtown Annapolis, MD

The long, interesting history of the Flag House Inn

The two townhouses comprising Flag House Inn were built in 1879 and served a number of roles through the years. Descendants of the original builder say it passed through several generations of their family well into the 20th century. Each house in the duplex was individually owned, and we have traced the ownership in State Archives/ property records back to the early 1900’s. 

The two townhouses eventually became boarding houses, we have been told by several visitors that occupants were typically young ladies known as “drags” in Navy slang, and the male Midshipmen would call on the ladies in the sitting room. No visitors allowed upstairs! This type of arrangement faded over time, and women were initially admitted to USNA starting in the mid 1970’s and now make up ~30% of each class. At other times, the houses were owned by families.

In 1992, the family owning #26 Randall St purchased #24 and converted it into a bed and breakfast and the exterior appearance that largely resembles what you see today. In 1997, Charlotte & Bill Schmickle purchased the properties and ran the inn for 21 years, developing it into the well-appointed B&B that guests will experience today. It has been decorated with love and attention to historical detail. Every item in Flag House Inn has a story behind it!

Since early 2018, Flag House Inn is now owned by Marty & Carmel Etzel, who have entered the business after careers in the corporate (Marty) and education (Carmel) worlds. They bring their many experiences from personal & business travel, property management, marketing and a deep knowledge of Baltimore, Washington DC and the Eastern Shore, and can make many recommendations on what to do in and around Annapolis.

While keeping the traditional decor that’s appropriate to downtown historic Annapolis, they are working on modernizing many aspects of your experience such as room amenities, breakfast, and starting new traditions.

Many of our past visitors greatly enjoyed their stay with us, see the reviews of some of these past guests.

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