Our spacious common areas and carefully designed guest rooms offer tranquility mere steps away from the award-winning restaurants and nightlife of Annapolis. Our deliberate interior design incorporates original architectural features with fresh furnishings of the highest caliber. Every detail was carefully selected in order to deliver a uniquely memorable guest experience that reflects the character and history of Annapolis.
Set in an 1879 architectural masterpiece, the hotel was originally built by Welsh shipbuilder, Richard Owen Williams, as two personal residences. Blending historic beauty with the amenities of today, the hotel has been meticulously restored to provide you with a carefully curated stay, while maintaining the original architectural details of the duplex home.
In the hotel’s Parlor Room , you will find no detail overlooked. The furnishings evoke a sense of 19th Century formal elegance. Located above the busy sidewalks of Randall Street, the lounge offers a wondrous and quiet respite for you to recharge, unwind, and delight in the refined sophistication of the Flag House Inn.
Hotel guests dine on the antique table tops in the hotel’s dining room that includes original design elements like crown molding and a three-dimensional fireplace.
The Reading Room is a peaceful and exclusive retreat located on the hotel's first floor where guests may sip, savor, and indulge in this quintessentially Annapolis room defined by its bold colors and tastefully elegant design.
For the most important meal of the day, you will enjoy chef-prepared and locally-sourced breakfast items that will prepare you for an exciting day in Annapolis.
What you’ve heard is true! With Annapolis’ historic buildings that date back centuries, brick-lined streets, endless charm, and an unmatched culinary scene, you’ll find out quickly why Annapolis has been voted one of the most beautiful towns in America by Conde Nast Traveler. Our team is eager to offer our insider experience and help you uncover the best of our city.