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Flag House Inn

24 Randall St , Annapolis, MD 21401-1720 USA (Show map)
79 Reviews
$160 - $300
per night

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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
  • Dining4.7

Score Breakdown based on
79 Reviews

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Tastefully Appointed Inn

4.6 on October 11, 2014

Annapolis is a quaint city and has many options for B&B's. I selected the Flag House Inn based on it's price, location and description. I was not disappointed! The whole house was beautifully decorated and my room (Far East) exceeded my expectations in terms of size and comfort. One of the selling points is that the house has off-street parking and is conveniently located for walking to the historic points of interest and a variety of restaurants in the historic city center. While I originally booked a 3 night stay, I had to cancel the first night in order to attend a funeral; the hostess graciously agreed to modify my reservation without a cancellation fee or adjustment to the rate, which she probably could have insisted on. I appreciate this consideration and would not hesitate to recommend this Inn.

The best in Annapolis

5 on September 30, 2014

Looking for a wonderful place to stay with family or longtime friends in Annapolis, MD.? If so don't miss the Flag House Inn! Our 50th Reunion stay for five couples, all close friends since our entrance into the Naval Academy in 1960, couldn't have been better. Located just outside Gate one at the Academy. How great it was to park the car at the Inn and not have to take it out again for the duration of our three day stay. It is so centrally located you are within walking distance of all the Naval Academy and downtown Annapolis have to offer. The accommodations are superb, breakfasts wonderful and prices more reasonable than most in Annapolis. Highly recommended! We look forward to our next visit. Bill and Suzanne Dell

Centrally located Flag House Inn is charming

4.8 on September 26, 2014

We sojourned in Annapolis for 3 days recently and stayed at the Flag House Inn. Once we parked our car, we walked everywhere as the Inn is very close to Historic Annapolis, the Naval Academy and dining/shopping locations! The Inn is very charming and quiet...the host and hostess are wonderfully helpful people with many suggestions for enjoying our time in Annapolis.

Friendly hosts, wonderful breakfast, and great location!

5 on September 14, 2014

I was in Annapolis to visit my son at the Naval Academy. The Flag House is located right across from the Naval Academy, which was very convenient. Charlotte and Bill made us both feel right at home. We both enjoyed our delicious breakfasts, our comfortable room, and weekend together. I am looking forward to staying at the Flag House again in the future and would highly recommend it to others.

Perfect weekend in Annapolis

5 on September 01, 2014

Charlotte and Bill are the perfect hosts, always available yet not intrusive. Separate entrance for B&B allows privacy but our hosts are always easily accessible. Rooms immaculate and charming. Location is perfect for two block walk to restaurants shopping and dock. The best B&B experience you could hope for!!


5 on August 20, 2014

We stayed for a weekend in early August and it could not have been better. Outstanding location for Academy and DTA. Wonderful hosts!

Amazing B&B

5 on August 17, 2014

We stayed here during parents weekend at the Academy and it was perfect. The hosts are great people and the house is a beautiful historic home. Was the perfect fit for us. We will definitely be returning. Highly recommend this B&B.

Would be hard to top the Flag House Inn

5 on August 12, 2014

Haven't stayed in a B&B in a long time. So glad we picked the Flag House Inn as our reintroduction to the B&B world. The location was perfect, located close to everything. The Inn is beautiful, as was our room. We had the Commodore room which was so spacious, quiet and very comfortable. Breakfast was oh so good! Bill and Charlotte were the perfect hosts, Would love to go back.

Couldn't Be Happier

5 on August 02, 2014

Let me start off by saying, we had a wonder full time here. My wife and I decided to go for Annapolis for our honeymoon, and we couldn't be happier with where we chose to stay. The Flag House Inn is perfectly located near(within easy walking distance) all the historic sites of Annapolis as well as lots of good dining. Our room was extremely clean and comfortable with plenty of space. The owners, Charlotte and Bill, were extremely kind and helpful. They had lots of great suggestions for things to do in the area, and were always more than happy to help or answer any questions. The atmosphere at breakfast was always warm and amiable, and the conversations always made it feel like we were staying with friends. The breakfasts were delicious, and the owners were always more than happy to accomodate any special dietary needs (though we didn't have any, and enjoyed everything they served - they were always sure to ask and offer alternatives to guests who did). Also the fact that the Inn has its own parking is very convenient, and made our excursions from it easy and smooth. All-in-all we had and amazing time, and our stay at the Inn was all we could have hoped for. We would highly recommend it, and would love to return!

Wonderful place to stay in Annapolis

5 on August 01, 2014

Stayed for a girl's weekend and had a wonderful time. The owner's were lovely people and run a clean and nicely decorated Bed and Breakfast. We would definitely stay here if we travel to Annapolis again. The location is perfect and within walking distance of town and restaurants/bars. No need to take your car anywhere!

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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, In-room internet, Fax Machine, Fireplace, Library, Telephone, Wi-Fi , 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



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

Property highlights

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