We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Flag House Inn

Certificate of Excellence
GreenLeadersBronze level
Hotel website
26 Randall St, Annapolis, MD 21401
Special Price
Mon-Wed 2 night 10% off
Book on
TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Prices from our online travel partners are not available
We can't find prices for this hotel
Our online travel partners don't provide prices for this accommodation, but we can search other options in Annapolis
Check In Check Out
Show Prices
Management photos
Flag House Inn
View Map
Add Photo Write a Review

326 Reviews from our TripAdvisor Community

Rate and write a review
Roll over, then click to rate
  Click to rate
Traveler rating
    296
    27
    1
    2
    0
See reviews for
61
192
9
7
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (69)
Date | Rating
  • Dutch first
  • English first
  • French first
  • German first
  • Any
English first
  • All months
    (326)
  • Mar-May only
    (75)
  • Jun-Aug only
    (138)
  • Sep-Nov only
    (82)
  • Dec-Feb only
    (31)
All months
Arlington, Virginia
1 review
5 of 5 stars Reviewed 2 days ago NEW

We stayed at the Flag House Inn this past weekend and were very pleased with our experience. Charlotte and Bill were very welcoming and made us feel right at home. We only saw them briefly upon arrival, and then again in the morning, but they were very pleasant to be around and accomodating. The Inn is in a great location-... More 

Was this review helpful? Yes
Germany
Level Contributor
19 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed 1 week ago

We had an excellent stay at the Flag House Inn. Charlotte and Bill were so welcoming. We really felt home from the first minute of our stay. The Flag House inn is located close to downtown, all in walking distance. We stayed in the Fleet Suite which is very spacious and lovely decorated. We, above all our son, loved Bill's... More 

Was this review helpful? Yes 1
Durham, North Carolina
1 review
5 of 5 stars Reviewed 1 week ago

We found the best place to stay in Annapolis. Charlotte and her husband were so welcoming. The location was fantastic... Close to downtown and the water yet quiet and comfortable. We know where we will be staying the next time we are in town.

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

Always great to welcome fellow "Durhamites" to our home. So happy you enjoyed your stay with us and we would welcome you back anytime you find yourselves in Annapolis again. More 

Dallas, Texas
Level Contributor
6 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 1 week ago

We had an excellent stay at the Flag House Inn. The welcome from Bill and Charlotte started our vacation with a warm smile and many interesting stories. The room was spacious and quiet. the common areas very welcoming. The whole house is very tastefully decorated without being overbearing. Everything is spotless and in perfect shape, like if it had just... More 

Was this review helpful? Yes 1
charlotteofFHI, Owner at Flag House Inn, responded to this review

Anyone who has stayed with us knows that conversation and stories are part of the guest experience at Flag House Inn. We love sharing our knowledge of the area as well as the many facets of our lives before becomining inn owners. But, we also love to hear the stories of our guests which help us learn about places to... More 

Frederick, Maryland
2 reviews
5 of 5 stars Reviewed 2 weeks ago

Innkeeper Charlotte's first words to us as we entered were: Welcome to our home. Immediately we felt at ease and truly welcomed to a lovely home. Our third floor room was well appointed as the Far East Room with appropriate Asian décor. The bedroom and bathroom were clean and bright with all the amenities we expected. Very quiet HVAC system,... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

Isn't it wonderful to have a place to visit and not have to use your car for several days. That is the joy of Annapolis! More 

Irvine, California
1 review
5 of 5 stars Reviewed 3 weeks ago

I can't imagine a better place to stay in Annapolis than Flag House Inn. The location is ideal for seeing the city. The inn is lovely and spotless, peaceful and very relaxing. Charlotte and Bill are delightful, welcoming hosts--and Charlotte can really cook!!! The breakfasts were delicious. Both Charlotte and Bill are willing to go above and beyond to help... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

We, too, enjoyed meeting you and sharing some of our knowledge of the area with you. Wishing you son all the best in his new job and, who knows, you might just have to come back here to the "right" coast and visit him again before too long. :-) More 

Los Angeles, California
Level Contributor
6 reviews
5 of 5 stars Reviewed 3 weeks ago

Returning to the Flag House Inn this August was a treat! Charlotte and Bill are wonderful hosts! The rooms are immaculate and comfortably appointed, the breakfasts are delicious and beautifully served, and the location cannot be beaten with the Naval Academy directly across the street and all of downtown within easy walking distance. The conveniences of on-site parking and free... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

Over the years it has been such a pleasure getting to know you. Although we are so happy that your son's years at USNA are complete I know I will miss not seeing you from time to time but am so happy that our paths have crossed during his "fours years by the bay." More 

Evesham, New Jersey
1 review
5 of 5 stars Reviewed 3 weeks ago

My husband and I stayed at the Flag House Inn in Annapolis for our 12th anniversary and had a wonderful experience. The location is perfect, as it is a block from the downtown area, yet still preacful and quiet. We enjoyed beginning and ending the day sitting on the front porch. Bill and Charlotte are wonderful hosts and make you... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

We are so happy you enjoyed celebrating your 12th anniversary here in Annapolis and at our B&B. Viewing the Water Witch tower was especially significant for a fireman and spouse! :-) Many more wonderful years together and, hopefully, return visits to Annapolis. More 

1 review
5 of 5 stars Reviewed 3 weeks ago

Charlotte and Bill did an excellent job to help make our visit to Annapolis one to remember! They are extremely knowledgeable about the area and did everything they could to make sure our trip to Annapolis was as enjoyable as possible. They were a great resource in suggesting activities and restaurants nearby. Our room was clean, quiet, and very welcoming.... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

Tim you hit the nail on the head! A B&B (in my humble opinion) should be clean, welcoming, have hosts that are knowledgable about the area, have good breakfast offerings and the best of all have great guests that like to talk to each other in the morning. Location, of course, is so important also but all of the above... More 

Fernandina Beach, Florida
1 review
5 of 5 stars Reviewed 3 weeks ago

My husband and I flew in at the last minute to visit our son who was in town, on vacation, for just a few days. Based on the rave reviews right here on Trip Advisor, I called hostess / owner Charlotte to check on availability and had a delightful conversation, booking the one and only room left, on the third... More 

Was this review helpful? Yes
charlotteofFHI, Owner at Flag House Inn, responded to this review

As you know, we really enjoyed getting to know you and meeting your son while he was stateside for a visit. Always great to have folks from northern Florida for Bill to reminisce about the area around Jax and how it has grown. More 

Questions? Get answers from hotel staff and past guests. Ask a question

31 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (26)
Viewed
Hotel & grounds (7)
Viewed
Room/suite (4)
Viewed
Dining (3)
Viewed
Bathroom (2)
Viewed
View from room (4)
Viewed
Other (6)

Management photos: Courtesy of the property manager

Viewed
All management photos (5)
Viewed
Hotel & grounds (4)
Viewed
Room/suite (1)
Check In Check Out
Show Prices
Hotels you might also like...
Travelers also viewed these Annapolis hotels
0.2 mi away
Historic Inns of Annapolis
Historic Inns of Annapolis
#5 of 21 in Annapolis
4.0 of 5 stars 776 reviews
0.7 mi away
Loews Annapolis Hotel
Loews Annapolis Hotel
#3 of 21 in Annapolis
4.0 of 5 stars 835 reviews
0.2 mi away
Annapolis Marriott Waterfront
Annapolis Marriott Waterfront
#10 of 21 in Annapolis
4.0 of 5 stars 87 reviews
Show Prices
Show Prices
Show Prices
0.8 mi away
O'Callaghan Hotel Annapolis
O'Callaghan Hotel Annapolis
#12 of 21 in Annapolis
4.0 of 5 stars 629 reviews
1.0 mi away
Westin Annapolis
Westin Annapolis
#9 of 21 in Annapolis
4.0 of 5 stars 611 reviews
3.4 mi away
SpringHill Suites Annapolis
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities