Looking for an Annapolis gem of a B&B? Look no further than the Flag House Inn located in Maryland’s historical capital. My first encounter with this lovely inn was when my husband and I stayed there a few years ago. Since then, two ambitious 2011 U.S. Naval Academy graduates purchased and carefully renovated it. They added a spacious, cozy reading room within the footprint – providing additional space for guests to relax when not exploring the town. I recently visited again to chat with the manager and view the enhancements. The guest rooms and common spaces have been entirely transformed with deliberate interior design choices focused on creating an inviting and restful experience. Today, the Flag House Inn offers tastefully elegant spaces that provide modern comfort while acknowledging the property’s history and place in this delightful town with such a rich nautical history.
Flag House Inn | 26 Randall Street, Annapolis, Maryland | website | 410-280-2721
Flag House Inn certainly earns its name. The property flies flags from the states and countries of its guests. So when you’re there, you’ll immediately figure out from where your fellow guests hail just by looking at the flags hung from the front porch.
The group that owns the Flag House Inn has other recently renovated historical properties close by, so if your traveling party is large, you’ll surely find accommodations for your group.
DISCLAIMER: My husband and I have stayed in many properties in our travels, but a few stand above the rest — this is one of them. We have not accepted free trips, endorsements, or gratuities from the owners. All the opinions and photographs featured on this page are my own. I simply share this property profile because it was unique in its location and hospitality, so I think others may consider staying there as well. Happy travels!
Why Flag House Inn?
- Flag House Inn is in a perfect location for enjoying Annapolis. It is across the street from one of the primary entrances to the U.S. Naval Academy and less than two blocks from the center of town and the City Dock. Great restaurants and interesting shops are close by. Once you park your car and check in, you will most likely spend the rest of your stay in town on foot—the town is that walkable.
- There are six guest rooms, and some accommodate up to four guests. All guest rooms offer complimentary high-speed Wi-Fi, flat-screen TVs, and complimentary breakfasts.
- The common spaces are wonderfully designed for relaxation. The Parlor and the Reading Room offer comfortable upholstered seating that invites guests to dig into a good book, do some work on their laptops, chat with others, or simply…relax. The Dining Room has round tables that seat 2 to 4 guests, so traveling parties can easily sit together.
- Breakfast! Creative and delicious! The “most important meal of the day” is served each morning in the Dining Room. (With full bellies, we set off each day and didn’t need to stop for lunch — although we did pause for afternoon snacks from local watering holes. 😁)
- Their communication is proactive and helpful from the beginning of the reservation process through check-in and all the way through to check-out. I experienced the same level of communication before planning my recent visit. I received prompt responses to my emails and was warmly welcomed upon arrival.
- Flag House Inn aims to please. They are happy to help you plan your stay in town, including key places to visit, unique shops, and great dining spots. To get a jump start on your visit to Annapolis, check out Flag House Inn’s website, which profiles the area and its attractions.
History of Flag House Inn
Flag House Inn began as two independently owned duplexes built in 1879. In 1992, the two homes were merged into one dwelling, so the interiors of both places were joined, and the property began its life as a B&B.
After changing ownership over the years, two 2011 U.S. Naval Academy graduates purchased the Flag House Inn in 2022 and extensively renovated it. Their hospitality group includes other nearby properties named for their locations: 134 Prince Street, 86 State Circle, and 1313 West Street.
Follow Flag House Inn on social media, and you’ll gain a better understanding of the inn and the area (plus mouth-watering pictures of their bountiful breakfasts!).
Things to Do in the Annapolis
Annapolis is the perfect spot to stay for a weekend or even longer if you’re lucky. Use this guide to discover your activity options while staying in Annapolis.
Nearby Attractions
In addition, Annapolis makes a great home base for exploring nearby spots such as Washington D.C., Mt. Vernon, southern Maryland (including Historic St. Mary’s City and Solomon Island), St. Michael’s, and beautiful parks with hiking and biking trails.
Final Thoughts
Our stay at Flag House Inn was central to our enjoyment of our visit to Annapolis. This place offers a top-notch location, hospitality, and helpful, friendly hosts. Enjoy your stay!
