Flag House Inn

White colonial style sign for St Johns College

Check Availability

Annapolis Lodging Specials & Packages

Meeting the Needs of Your Group

Naval Academy visits, team meetings, sailing schools, sporting events or history, vacations, romantic weekend getaways, business and retirement travel: whatever brings you to Annapolis, Maryland, Flag House Inn is your best base of operations with free off-street parking and great accommodations.

We can line up private meeting space nearby if you need a larger space to meet or want to have a private event.

Contact us to work out a custom program to meet the needs of your group.

Cadets from the Naval Acdemy walking down a path

Naval Academy Visits

Flag House Inn has THE best location for visiting the US Naval Academy:

  • Located directly across from main gate to Naval Academy.
  • On-site parking at no extra cost.
  • Owners are sponsor parents and can offer insight based on their experiences.
sailboats in a harbor

Sailing & Powerboat Schools and Boat Shows

  • Spring Boat Show
  • Fall Boat Shows
  • J-World
  • Annapolis Sailing School
  • Chesapeake Sailing School
  • Annapolis School of Seamanship

At Flag House Inn, Enjoy the Best of Both Worlds:

  • Centrally located for the sailor – walk to your location while enjoying off-street parking.
  • Relax in the heart of Annapolis’ nightlife.
  • Walk to the best pubs and restaurants in town.
  • Walking distance to the U.S. Naval Academy, and many of the sail & power schools.  Some are a short drive away.
  • 2 blocks to City Dock: Annapolis’ maritime center since 1696.

At Flag House Inn, you enjoy on-site parking at no extra cost, a delicious breakfast to start your day, king-size beds, private bathrooms, Wi-Fi, air conditioning and cable TV.

Discounts:  We offer 10% off published rates to Annapolis School of Seamanship when you are staying (off season Thanksgiving to Easter).  Larger discounts available in off season for instructors. We also offer off season discounts for sailing school extended stays (3 or more days not including weekend days or major event weeks).

Sign for St Johns College

St. John’s College

Flag House Inn is located three blocks from the College campus. We welcome alumni, parents and friends of current students.

Admissions Visits: We can identify any off-peak pricing or timings to plan your trip. If you are a party of 3, we have a suite, so the family can stay together. 

Flags flying from white porch with hanging flower baskets

Tourism & Events (Birthday / Wedding / Anniversary)

Flag House Inn is noted for comfort, quiet, security & convenience.  We are the ideal place for the quality conscious traveler while still offering great value:

  • Priced competitively with other Historic District inns and hotels with similar features (parking & breakfast included here)
  • Free parking on site: compare with hotel parking charges and limited on-street parking (2-hour maximum)
  • Full breakfast with all the trimmings and 24/7 coffee & tea on the go
  • Insider’s advice on the best deals in town for lunch, dinner, boat excursions, tours, and so much more.

Plus: The peace & privacy advantages of a private historic home and personally owned and operated by your hosts.

Retiree Advantages: We’re close (within 4 blocks!) to everything.

Ease of coming & going: A great advantage in rainy, hot or cold weather, or during a busy day. 

Aeriel view of the Maryland State House

Historic District Tourism

The Flag House Inn Advantage:

  • An authentic & historic bed & breakfast inn, not a hotel, located in the colonial waterfront sector of Annapolis.
  • Historic Victorian in the National Historic District.
  • On-site parking at no extra cost.
  • Members of the Historic Annapolis Foundation.
  • Closest to the U.S. Naval Academy.

Within 3 Blocks – The Heart of the Colonial Area:

5 of the finest Georgian colonial mansions in America:

  • William Paca House & Gardens (1763), museum
  • Hammond-Harwood House (1774), museum
  • Chase-Lloyd House (1769), open to the public
  • McDowell Hall (1744), St. John’s College Campus
  • James Brice House (1767)

25 significant colonial buildings dating to 1680, such as the Maryland State House (1772 – open to the public) and scores of other colonial, federal, and Victorian buildings.

Find the ideal walking, bus or boat tour, we have the latest Annapolis historic guidebooks and pamphlets and can provide the insider’s recommendations on area day trips.

Elegant dining room table set ready for breakfast

Business Meetings and Executive Retreats

Meeting space available with full house rental.

We can work with you based on the needs of your group either onsite or at private meeting space nearby.  We can also work on room placement with neighboring B&B’s/ Inns and other accommodations.

We can offer competitive pricing, and besides our prices include parking and breakfast, unlike the big hotels in town.

Marty had considerable experience in the corporate world with training & events, and will work with you to tailor our support to your unique needs.


Team Up with the Schooner Woodwind: This two-masted purpose-built schooner, sailing from City Dock, specializes in corporate charters and exciting team-building sailing exercises—a perfect way to begin or end your retreat at Flag House Inn!

Maryland State House - large brick colonial-style building surrounded by trees

Legislative Session

If you are involved in the Maryland Legislative session running January to mid-April, we can develop a tailored package for your needs, whether it is a block booking or an a la carte package.


No matter if you are a legislator, staffer, lobbyist or consultant, you’ll find Flag House Inn is a quiet and secluded base for your busy time in Annapolis. We’ll provide breakfast and can work with you on any other needs you may have, including meetings and events.

Book Direct for Best RateGet the best rates & attention to your needs when booking on our site!Get Best Rate
alp logo
select registry logo
trip advisor logo
Maryland Green Registry Member
You Tube Logo
Trip Advisor travelers choice winner logo