Flag House Inn

24 Randall St , Annapolis, MD 21401-1720 USA (Show map)


The perfect location with on-site parking, king or twin beds, private baths, comfortable seating, good lighting, and in-room cable TV. On the block connecting the historic waterfront and the U.S. Naval Academy in the National Historic District, Flag House Inn offers five guest rooms (including a two-room suite). Splendid interiors are filled with original naval and nautical art and memorabilia, fine paintings, antiques, and reproductions. The large front porch, flying the state or national flags of guests, greets you with swings and teak benches. Enjoy a large, hot breakfast before visiting Flag House’s beautiful and historic neighborhood.



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  • Guest room4.8
  • Service4.9
  • Value4.6
  • Cleanliness4.9
  • Onsite Dining4.7

Best B&B in Annapolis

5 on October 25, 2016

Our favorite B&B in Annapolis, MD is the Flag Housr. The owners are gracious hosts who provide a wonderful cooked breakfast with a nice selection of teas, coffee, cereal etc. The 5 rooms, one of which is a suite with an extra single bed, are distinctive in decore and are tastefully furnished and fully equipped. We were very comfortable. In a town where the streets are narrow and traffic can be heavy, their location not only provided off street parking for each room, but is centrally located to downtown Annapolis, but less than a block walk from the main entrance to the U.S. Naval Academy. There are numerous publicatiosn in he common room to assist a newcomer with what to see and the history of Annapolis. We feel like we are coming home with each visit. The owners are very well educated, excellent conversationalists with wonderful stories and insights to share. They are parents of a Naval Academy graduate and thus able to share an intimate knowledge of the Academy and the town. You should make reservations very early as they can book up fast.

Gracious Hosts

5 on October 04, 2016

Our family stayed at Flagg House Inn in September for one night. We rented three of the rooms and found them all to be clean quiet and comfortable. The house itself is located in a wonderful area of Old Annapolis, very convenient for sightseeing in town or on the bay. Off street parking behind the house is a definite plus. The common interior rooms are also very comfortable and nicely appointed. Here you will find a wealth of information about the area's history and the local sites. I also found the in room information binder to be very organized and helpful. That said the best source for information would be the hosts themselves. Bill and Charlotte are very welcoming and Charlotte gave generously of her time to help us get the most out of our short stay. Breakfast was delicious thanks to Charlotte and she happily accommodated our daughter's food restrictions. We would definitely look forward to staying at Flagg House Inn in the future!

The Innkeepers at The Flaghouse made our stay memorable!

5 on August 30, 2016

We can't say enough about our experience at The Flaghouse Inn. Bill and Charlotte are great people and you can tell that they want your stay to be everything it can be. Location is fabulous, literally accross the Street from the academy and just a short walk to the roundabout which is the center of town and the start of many great bars and restaurants. Bill and Charlotte were most helpful with reccomendations for dinner and steered us to The Annapolis Ice Cream Parlor, serving absolutely decadent hand made ice cream. The Inn is an historic property in immaculate condition. Breakfast is prepared by the owners and was excellent. Make this your place to stay when you visit the beautiful town of Annapolis!

Truly A 5 Star B&B

4.0 on August 26, 2016

We stayed at the Flag House Inn for four nights during Plebe Parent Weekend mid-August 2016. Charlotte & Bill are fabulous innkeepers in every way imaginable. Their attention to details and our needs went over and above. We were there during a heat wave and the rooms were very cool (great AC), always ice and water available etc. A delicious-full breakfast was served promptly and accommodated our morning schedule each day at the USNA. A very clean and well appointed B&B. The other guests were very pleasant to visit with too. On-site parking is a huge bonus! Charlotte made fantastic dining recommendations. We will definitely return to the Flag House Inn. Cynthia - Middletown, NJ

Flag House was Fine

4.8 on August 20, 2016

We enjoyed our stay for a number of reasons - excellent location, friendly and helpful proprietor, lovely and clean facilities, wonderful breakfasts!

Location, location, location!

4.4 on August 20, 2016

If you're looking for convenience to the Naval Academy, this is the place - right across the street from the main entrance. A delightful inn with delightful owners. Charlotte and Bill pay attention to every detail of your visit. They even hang your state flag for the duration of your stay. Breakfasts are delicious. Definitely will return.

Lovely experience!

3.8 on June 28, 2016

Stayed here with a friend for a quick overnight. Proximity to USNA is fantastic - it is literally right across the street! Also within easy walking distance to downtown shopping and dining. Fantastic parking - Bill parks your car for you - an added plus. Breakfast was tasty and we were treated to a lively, interesting discussion on international politics for no extra charge ;-). A great stay!

Wonderful Hosts!

5 on June 28, 2016

Bill and Charlotte are the most friendly, helpful, and accommodating hosts and made me feel very comfortable and welcome in their lovely B&B. Both go out of their way to keep things easy for their guests, so that guests can truly relax and enjoy every moment of their stay. The inn itself is in a great location, is very clean comfortable, and no detail is left unattended. Parking is essential and the inn provides several free spaces. A truly lovely B&B.

Annapolis Delight

5 on June 08, 2016

The Flag House Inn has a superb location, and Charlotte and Bill took a keen interest in guiding us to sights and restaurants they thought we would enjoy, hitting the bulls-eye with each recommendation.

Let's stay another night

5 on June 05, 2016

Very convenient location with on-site parking and surprisingly quiet. The breakfasts are varied and tasty. The hosts are helpful with suggestions for meals and activities and are very knowledgable about Annapolis. The house is nicely appointed; the common room and our bedroom were inviting. We found ourselves extending our stay in Annapolis because the Flag House Inn was such a delightful place to be.

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Rooms & Rates

King or twin bed rooms

Our four guest rooms accommodating up to two guests have either king or twin beds, cable TV, private bath, comfortable seating and good lighting for reading.

  • Maximum Capacity: 2
  • Bathroom Private Bath

Two-room suite

Our two-room suite occupies the entire second floor of one of the paired townhouses that comprise Flag House Inn. The front room has a king Hickory-White pencil-post bed, love seat, wing chair and cable TV. The back room has a twin bed, large Hickory-White couch, wing chair and cable TV. There is an en suite private bath.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King , 1 Twin

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Location Type

Chesapeake Bay, Downtown, Small town


Baltimore, MD (BWI-Baltimore Washington) 20 miles

Directions to property:

From I-95 or I-495 from Washington, DC, or I-97 from Baltimore, exit onto MD 50 east toward the Bay Bridge. Exit MD 50 at exit #24 Rowe Blvd (bear to right at end of ramp). At second traffic light turn left onto Taylor Avenue. Go two blocks until Taylor Avenue dead ends and bear to the right. After going through the curve turn right at the traffic light. You will now be on King George Street (no street sign at this point). Go to end of King George St. and turn right onto Randall Street (at Naval Academy gate). Flag House Inn is the 8th house on the right. Turn into driveway and come to the front door of #24. From the Eastern Shore of Maryland Take Hwy 50 West to exit #27 (to USNA). At very end of exit ramp turn left. Continue straight and cross the US Naval Academy Bridge. At the second traffic light turn left onto King George Street (no street sign at this point). Go the the end of King George St and turn right onto Randall Street (at USNA main gate). Flag House Inn is the 8th house on the right. Turn into driveway and come to the #24 front door.

Area Attractions

Antique Shopping, Art Galleries, Concert venue, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, National/State parks, U.S. Naval Academy, Chesapeake Bay, Maryland State House, St. John's College, William Paca House, Hammond Harwood House, Outlet Stores, Performing Theater, Picnic area, Religious Services, River

Inn Details

Establishment type

Private Home Bed and Breakfast, Bed and Breakfast, Urban Inn, Historic Inn

On-site amenities

Board games, Copier, Fax Machine, Fireplace, Library, Telephone, Wi-Fi, Wired internet , on-site parking, porch, swings

Room amenities

Air conditioning, Alarm clock, Ceiling fans, Desk, Hairdryer, Ironing Board, Radio, Satellite/Cable TV, TV

On-site activities

Bicycle rental, Bird watching, Boating, Canoeing, Fishing, Golfing, Hunting, Kayaking, walking, running, segway tours, Sailing, Shopping, Sight-seeing

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  • Check In:: 4:00-6:00 p.m.
  • Check Out:: 11:00 a.m.
  • Open All Year Round: Yes
  • Smoking Allowed: Outside only On front porch only
  • Drinking Allowed: Yes
  • Alcohol Provided No
  • Suitable For Children: Limited
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Minimum Stay: Most weekends @ two-nights, longer for special event weeks
  • Accepted payments VISA, Mastercard, Personal checks, Travelers checks, Cash
  • Deposit Amount Required: One night's stay or 50% for special events
  • Cancellations: No-shows or cancellations within 10 days of arrival date will be subject to the full rate for the full stay or any portion that cannot be re-booked. A minimum of $25.00 per room processing fee will be charged for any cancellation.



Charlotte & Bill Schmickle

Languages spoken


About the innkeepers

Bill and Charlotte enjoy walking in historic Annapolis, reading and fine dining, interior design, Navy sports and boating with friends. Bill is past chair of the Annapolis Historic Preservation Commission.

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  • Time Served: 8:30-9:30
  • Serving Location: Dining Room