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26 Randall St, Annapolis, MD 21401
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10% off room rate
Flag House Inn
Ranked #2 of 31 Annapolis B&B and Inns
Certificate of Excellence 2014
GreenLeadersBronze level
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274 reviews from our community

Traveler rating
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Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    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
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Fort Worth, Texas, United States
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars

My wife and I stayed at The Flag House Inn last week as our son was visiting the U.S. Naval Academy. In short, we loved our stay. The Flag House Inn was spotlessly clean and very cozy and comfortable during our very cold stay in Annapolis. Bill and Charlotte (the owners) are absolutely delightful and FULL of information about Annapolis... More 

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1 review
5 of 5 stars Reviewed 1 week ago

We are local Virginia residents who simply wanted to get away for a weekend with no car, relaxation and quiet. We found all of that at the Flag House Inn. Great location to downtown Annapolis, quiet and very relaxing. Charlotte and Bill are great hosts and the accommodations were fantastic. We will plan another visit soonest.

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Columbia, Maryland
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

We had a wonderful experience staying at the Flag House Inn. Our hosts Charlotte & Bill were tremendous inn-keepers, as well as being nice and ever so accommodating. The room we had was really spacious and comfortable, and the breakfast was outstanding. The location of the Flag House Inn is perfect - adjacent to the Naval Academy, and a block... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

We had cold weather for Valentine's Day weekend but the warmth in your hearts made it all worthwhile. So pleased you enjoyed you stay with us at our B&B and hope we can help you another time when you need some R&R. More 

1 review
5 of 5 stars Reviewed 2 weeks ago

I just wanted to thank Charlotte and Bill (the owners) for a great time this past weekend. What a great house. Our room was really nice and Charlotte and Bill were very gracious hosts. The location of the Flag House Inn is awesome!!! Right in the heart of downtown Annapolis. We parked our car at the house and didn't drive... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

Even with the cold windy weather you were able to have a great Valentine's Day weekend in Annapolis. We were so pleased to be part of your getaway and will look forward to having you back again in the future. More 

Hampton, Virginia
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed 4 weeks ago

We would like to take this opportunity to highly recommend the Flag House Inn in Annapolis, Maryland to anyone looking for upscale accommodations, adjacent to the Naval Academy, convenient to everything and hosted by a fun couple. Bill and Charlotte Schmickle have owned and operated the Inn for 14 years and obviously love what they do. We made reservations at... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

There is joy in my heart as well as in my voice when making resrvations for the wonderful guests that we have welcomed to our B&B these past 18 years. Meeting new people at breakfast is one of the best aspects of staying at a B&B and I am so happy your experience with us here at Flag House Inn... More 

Flemington, New Jersey
Senior Contributor
24 reviews 24 reviews
7 hotel reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed January 4, 2015

We stayed at the Flag House Inn 16 years ago on our first trip to Annapolis. Loved it then, loved it now. Rooms are extremely comfortable, breakfast was wonderful both days. Lots of choices. Location is perfect. Just down the street from the Naval Academy gate and downtown is the opposite direction 5 minute walk. Two touches that make this... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

It's always great to say "Welcome Back" to folks who have stayed with us whether a year or sixteen years ago. We hope to do so for you again! More 

Abington, Pennsylvania
1 review
5 of 5 stars Reviewed January 4, 2015

Spending a weekend just before the Christmas holidays was a wonderful treat at the Inn. Our hosts were so friendly and their inn was more like a second home than a place to spend the weekend. The breakfasts each day were delicious and varied and they made every effort to make us feel at home. That together with the holiday... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

We thank you for your very kind words about our B&B. It was our joy to welcome you to our home on a weekend packed with so much to do. Between Midnight Madness on Thursday and the Lighted Boat Parade on Saturday you had a full weekend to enjoy our town, your family and a quick trip to the Newseum... More 

Westport, Connecticut
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed December 29, 2014

From the moment I called and spoke with Charlotte I knew that we made the right choice. You could not ask for a more convenient Inn, especially since our main focus for our very quick but enjoyable stay was to visit the Naval Academy. Charlotte and Bill are the perfect hosts and great Annapolis Ambassadors - always willing to give... More 

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

Such a lovely way to start a new year with a review from you. I really liked your "Annapolis Ambassador" comment for we truly do love sharing the many wonderful things our town has to offer to all those great guests that come in through our front door. Wishing you and yours a very Happy 2015 and hope our paths... More 

Kailua, Hawaii
1 review
5 of 5 stars Reviewed December 29, 2014

Absolutely perfect in every regard. Booking was a breeze, arrival smooth and incredibly welcoming. Bill helped carry our bags in and situated our vehicle, which we did not have to drive the entire time we were there. Charlotte showed us up to our rooms and gave us a tour of the home. Having our state flag flown during our stay... More 

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charlotteofFHI, Owner at Flag House Inn, responded to this review

As you know, we, too, enjoyed meeting all of you when you were here for your 25th reunion. So glad you had a great time and a fantastic weekend reuniting with fellow USNA grads. Looking forward to 30th. More 

Boston, Massachusetts
Reviewer
3 reviews 3 reviews
3 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed November 25, 2014

Had a delightful weekend stay at the Flag House Inn. Charlotte was there to greet me upon arrival and Bill even helped me park my car (the spots are tight - but hey, cannot beat free parking!) and carried my suitcase to my third floor room. Did not spend a ton of time in the Inn, truthfully, because the location... More 

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

So glad you were able to easily get to see your friends as well as visiting USNA and our lovely downtown shopping area. It is nice when you live a busy life with lots of travelling to have a weekend getaway just to relax and reconnect with others. More 

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Additional Information about Flag House Inn

Address: 26 Randall St, Annapolis, MD 21401
Phone Number:
Location: United States > Maryland > Annapolis
Price Range (Based on Average Rates): $$
Number of rooms: 5
Also Known As:
Flag House Hotel Annapolis

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