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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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Mid week discount
Flag House Inn
Ranked #2 of 31 Annapolis B&B and Inns
Certificate of Excellence 2014
GreenLeadersBronze level
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250 reviews from our community

Traveler rating
    226
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40
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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
Traveler tips help you choose the right room.   Room tips (45)
Date | Rating
  • Dutch first
  • English first
  • French first
  • German first
  • Any
English first
Dallas, United States
Reviewer
4 reviews 4 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed yesterday NEW

We were visiting our son in D.C. and then spent the weekend in Annapolis. We choose the Flag House Inn because of it's location in the historic district and it's good reviews. We were very happy with our stay. The owners were super nice and accommodating. Our rooms were very comfortable and clean. The breakfast was wonderful, in fact I... More

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Brashear, Texas, United States
1 review
5 of 5 stars Reviewed 1 week ago

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... More

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

We so enjoyed meeting both of you but were thrilled the mids were granted two overnights for Labor Day weekend and your plebe got to be "free" for two days. What a fantastic treat that was for both of you. More

1 review
5 of 5 stars Reviewed 1 week ago

We only stayed at the Flag House for one night taking the chance to explore Annapolis in the afternoon and evening. I am sure we will return on our next trip to Maryland. Charlotte and Bill were fantastic hosts, giving us some great advice on where to go and see in our limited time and a really great restaurant recommendation.... More

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

So happy you found our lovely historic town and had a good visit. It is always our pleasure helping our guest find the best way to use their time in Annapolis as well as guiding you to some excellent places to eat. We look forward to having you back with us next time you are in town. More

Top Contributor
56 reviews 56 reviews
9 hotel reviews
17 helpful votes 17 helpful votes
4 of 5 stars Reviewed 1 week ago

Lots of steps in this B&B and the room was small with a bathroom lacking any charm compared to other B&Bs stayed at nearby. The owner has plenty of stories to tell so be mindful of your time or you'll get stuck in an overextended breakfast hour. On a positive note, the location is great with the Naval Academy gates... More

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

Yes, we do have two flights of stairs up to our third floor rooms but there really is not a place for an elevator in this 1880 home. I try to remember to tell guests when they are calling for reservations so they are not surprised by stairs - thanks for your comments as they reminded me to be sure... More

McLean, Virginia
Senior Contributor
34 reviews 34 reviews
20 hotel reviews
22 helpful votes 22 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We were in Annapolis to celebrate two family birthdays and found the Flag House Inn on Trip Advisor. We usually stay at B & B's and we wanted one that had availability for two nights over the weekend. We were really lucky to find the Flag House Inn. It is located right across from the Naval Academy grounds and about... More

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

I am so glad you had such a great birthday celebration weekend. Even the rains didn't interfere too much with all of your festivities. Wishing many more wonderful family activieis together in the future. More

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

My husband and I took a much needed overnight excursion and were blessed to find The Flag House Inn had an available room. We were graciously greeted by one of our hosts, Charlotte, who made us feel at home even before we stepped in. It was raining when we first arrived and Charlotte came out to greet us with large... More

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

Your kindness in writing such a wonderful review of our B&B is most appreciated. You really captured all that we try to do as B&B owners to help our guests enjoy their visit to Annapolis. It was a real pleasure meeting both of you and we hope you can come back another time to enjoy more of the sights and... More

Baltimore, Maryland
1 review
5 of 5 stars Reviewed 4 weeks ago

We were looking for a place to stay in the historic district of Annapolis to celebrate an anniversary. Looked into B&B's for the heck of it and this was one of the cheapest. At the time we made reservations, no one else had booked, so we started wondering what was wrong with the place. Actually, the Flag House Inn was... More

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

It was great having you celebrate your anniversary with us here at Flag House Inn. So pleased you enjoyed you stay, got the R&R you both needed and deserve and glad we did have others when you were here (from two room to full house each of the days) and that you found it so easy to book via our... More

1 review
5 of 5 stars Reviewed 4 weeks ago

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

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

We were so glad to host your stay for Plebe Parent Weekend. No for next four years and beyond it will be GO NAVY!! More

Corvallis, Oregon, United States
1 review
5 of 5 stars Reviewed August 16, 2014

In a selfish way, I am reluctant to give the Flag House Inn the fantastic rating they deserve. If everyone knew how great it is to stay there, I might not be able to get a reservation! We stayed with Bill and Charlotte over the 2018 Plebe Parents Weekend at USNA. I cannot imagine having better accommodations. The Inn is... More

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

We had a great time with our guests during PPW last week. As you know there is hardly ever a lull in the conversation around our breakfast tables. We'll look forward to having both of you back with us again. More

Lititz, Pennsylvania
Reviewer
5 reviews 5 reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed August 15, 2014

stayed at the Flag House for a long weekend in August. Hosts are convivial, and accommodations more than adequate for a long weekend. A longer stay, may lead to feeling a tad close as rooms are small. That said, there is much to see and do in Annapolis, so get out and WALK to everything!

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

We thank you for your review and glad you got out and about to see all the sights of Annapolis while you were here for a long weekend. Large rooms in an 1875 town home are hard to come by but that, too, is some of the joy of spending time in a home built over 130 years ago. 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): $$
Also Known As:
Flag House Hotel Annapolis

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