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All 31 Annapolis B&Bs / inns

Flag House Inn

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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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269 reviews from our community

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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
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Flemington, New Jersey
Contributor
12 reviews 12 reviews
7 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed 3 weeks ago

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 

Was this review helpful? Yes
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 3 weeks ago

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 

Was this review helpful? Yes
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 4 weeks ago

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 4 weeks ago

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 

Was this review helpful? Yes
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 

Maryland
Top Contributor
160 reviews 160 reviews
23 hotel reviews
99 helpful votes 99 helpful votes
4 of 5 stars Reviewed November 23, 2014

My wife and I had a wonderful last minute get-away before the holiday onslaught. The downtown location can't be beat, and on site parking included. The house is small, 5 rooms I think, and the owners live on site. Nicely decorated, quiet, and the proprietors took good care of us. Bill and Charlotte do like to talk, as some reviewers... More 

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

The holiday season is in full swing now and we hope you and your family had a lovely Thanksgiving Day together. Hopefully the quick getaway to Annapolis helped refresh you and will sustain you though the upcoming month of activisites. More 

1 review
5 of 5 stars Reviewed November 20, 2014

My husband and I thoroughly enjoyed our stay at the Flag House Inn. The B&B is a beautiful, nicely decorated and clean home. The location absolutely cannot be more perfect to view the grounds of the Naval Academy and downtown shopping. Bill and Charlotte are truly execellent hosts and have accomodated our every need. Even though we visited Annapolis before... More 

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

It was such a treat to have you stay with us after we met at another inn last September. B&Bs are such a great place to meet new and interesting people and I am glad you choose an overnight stay in Annapolis with us on your recent visit to our area. You are close enough to do it in one... More 

Johnson City, Tennessee
1 review
5 of 5 stars Reviewed November 18, 2014

I read nothing but great reviews on Flag House Inn in trying to choose a place to stay for our recent weekend trip to Annapolis and we were not disappointed! Our room was very nice and Charlotte and Bill were excellent hosts and provided us with great recommendations and everything we needed to make our stay a wonderful weekend. The... More 

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

I tried hard to get a win for Tennessee and Navy in their games this weekend but no luck there. Glad you enjoyed our breakfasts and your stay with us at Flag House. We, too, enjoyed meeting both of you and helping you enjoy a three day getaway to our area. More 

New Tripoli, Pennsylvania, United States
1 review
5 of 5 stars Reviewed November 18, 2014

My husband and I enjoyed our stay at the Flag House Inn, very much! Charlotte and Bill are A+++ hosts and made our annual "Mommy and daddy" weekend, one to remember. Accommodations were spot on. Breakfast was perfect. This Bed and Breakfast is clean, neat, comfortable and well decorated. Location to town and Naval Academy is the best! Overall we... More 

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

We were so pleased to be part of your Mommy & Daddy getaway weekend. It is always refreshing to have some adult time together without worrying about all the many things we do for our children each and every day. Sorry you had to leave before breakfast on Sunday but hope your daughter had a great experience trying out for... More 

Smithville, New Jersey
1 review
5 of 5 stars Reviewed November 6, 2014

We had a fantastic stay at the Flag House Inn. It looks exactly as the pictures on line. Very Clean and very comfortable. Charlotte makes the best breakfast ever! Both her and Bill are so welcoming and hospitable. Parking in back is great. So you can just park the car and forget about it. Close and walkable to everything, great... More 

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

Thanks so much for your kind comments about our home. We have been so lucky for the past 18 years to meet so many people just as sweet and interesting as both of you. Maybe next time I will be able to do more to make the weather more enjoyable. Ha Ha Thank goodness for the club level at the... 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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