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Flag House Inn

24 Randall St , Annapolis, MD 21401-1720 USA (Show map)
69 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.

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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  • Guest room4.8
  • Services4.9
  • Value4.5
  • Cleanliness4.9
  • Dining4.7

Score Breakdown based on
69 Reviews

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Flag House Inn

3.2 on July 21, 2014

My wife and I celebrated our wedding anniversary in Annapolis and enjoyed staying at Flag House Inn as part of that little getaway. The inn itself is perfectly located in the historic district of town, directly across from the Naval Academy entrance and the harbor area. It made getting around by foot very easy and quick forsight-seeing, restaurants,and nightclubs. The innkeepers Charlotte and Bill obviously take great pride in keeping their lovely inn in tip-top shape while extending warm but not intrusive hospitality to their guests. We recommend the Flag House Inn to anyone seeking to immerse themselves in the charms of historic Annapolis.

Have stayed here twice and loved it!

5 on June 06, 2014

My husband and I were in Annapolis to see our son who is attending the US Naval Academy and loved the convenience to both the academy and to walking downtown so easily. Also, the owners Charlotte and Bill are so friendly and full of great information about things to do in Annapolis and about the USNA. Charlotte also makes a delicious breakfast each morning and it was a pleasure meeting other guests. We felt very welcomed and comfortable in both our guest room and the common rooms of the B & B. They have lots of interesting books to read and Navy decor throughout the house to enjoy. It definitely felt like a home away from home and we highly recommend staying here!

Extremely pleased with our one-night's stay

4.4 on May 29, 2014

My boyfriend and I spent a night here during memorial day weekend and couldn't have been happier with our experience. The location is excellent; close proximity to the Naval Academy pedestrian entrance was ideal, as was the short walk to the downtown area. We tried to fit a lot into a one-day visit, and having a room at the Flag House Inn helped us do that (if we needed to run back to grab sunscreen or change it only took 5-10 minutes out of our day). Our room was originally a two twin bed setup, but Charlotte and Bill pushed them together for us to make one king-sized--we couldn't even tell it was two separate beds! Charlotte makes a mean pumpkin bread, too. We would certainly recommend the Flag House Inn to anyone visiting Annapolis. You couldn't beat the location OR the free parking, and the hosts are very gracious and eager to share their knowledge of the area.

Flag House Inn-wonderful, inviting and lovely!

5 on May 16, 2014

We stayed at Flag House Inn for my cousin's wedding at the Naval Academy. It was very quiet and beautiful. We especially enjoyed chatting with the owners who are very interesting people! The location absolutely can't be beat and best of all, they have parking there and it's very difficult to find parking in downtown Annapolis. It's easy to walk around the corner to all the best shopping and restaurants in downtown Annapolis. Best of all, you can walk back at night and rest on the front porch swing!

Girls Get Away

4.8 on May 15, 2014

I definitely recommend Flag House Inn! My childhood friend and I went for a girls weekend! Our room was perfect with 2 twin beds and was very clean, the food was great, and Charlotte and Bill were wonderful hosts. The location was perfect just a few minute walk right into downtown Historic Annapolis where there are countless restaurants and shops. Charlotte was very helpful with suggestions of where to eat and shop. Bill carried our luggage up to the room and parked the car. He even hosed off our car before we left for home because of all the pollen that was on it. Just wonderful people and I would go back in a heartbeat!!

Late April 2014

5 on May 01, 2014

What a pleasant surprise. Accommodations? The best! The food? excellent! Conversation? Didn't want to leave the dining room!

USNA Candidate Visit

4.8 on April 16, 2014

We were in Annapolis for our son's candidate visit at USNA. You could not have asked for a better location - directly across from the USNA entrance. The off road parking provided by the Inn was key for us and we were able to just walk everywhere. The room was spacious and very comfortable, the food was delicious, and the host/hostess were very helpful and friendly. In fact, we've already booked our stay to pick up our son from the USNA Summer Seminar in June. We hope to have many more visits to this lovely Inn and town.

Outstanding B & B

4.2 on November 19, 2013

Our room was such the pleasant surprise as it was even better than its photo! Bill and Charlotte have taken such care to create an ambiance so fitting to the lovely town of Annapolis. Charlotte prepared gluten-free foods so that I was never "on the outside looking in". Would definitely stay there again!

Annapolis visit

5 on November 05, 2013

In town to visit the Naval Academy and the location was awesome. Very convenient to everything in the old town area and permitted a walking environment. The owners were very pleasant and gracious hosts. The building was full of character and I thoroughly enjoyed my stay.

All too brief

4.8 on September 19, 2013

We were made most welcome by Bill and Charlotte who were the perfect hosts. The room was extremely comfortable and Flag House Inn is perfectly situated to explore Annapolis. All the accessories are of good quality and there are many thoughtful features. Our only regret is that one night wasn't nearly long enough.

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Location Type

Chesapeake Bay, Downtown, Small town


Baltimore, MD (BWI-Baltimore Washington) 20 miles

Directions to property:

From BWI take I-97 to Annapolis where I-97 terminates at MD 50. Take 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 you will 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 1). Flag House Inn is the 8th house on the right. Turn into driveway and come to the front door of #24.

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

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

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: Limited
  • Drinking Allowed: Yes
  • Guest Pets Allowed: No

Terms and Conditions

  • Minimum Stay: Most weekends @ two-nights, longer for special event weeks
  • 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


Details Diamond Collection

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

Property highlights

Get a free $20 gift card with every $100 purchase