Name: Flag House Inn
Address: 24 Randall St, Annapolis, 21401, US

10/10

Exceptional

14 Apr 2026

Tyler

Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast.

Self

8/10

Excellent

09 Apr 2026

Lorraine

Breakfast items were tasty and fresh but something besides sweets would have been nice, such as yogurt, eggs, and nuts. Our room was small but has a bench, desk, full mirror. The bed was comfy but very squeaky. The staff was friendly and helpful. Easy check in and out.
Parking was $50 a night which was nuts. Plenty of garages in the area that would allow you to park for a fraction of that. Excellent location. Quiet and safe with tons of shops and cafes in walking distance.

Partner

10/10

Exceptional

03 Apr 2026

Nathan

Great location. Beautiful room and exemplary service.

2/10

Poor

28 Mar 2026

Richard

The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house.

Partner

6/10

Pleasant

25 Mar 2026

Demetrios

The main house was very nice! Unfortunately, when I book, I wasn’t told that I would be staying in a separate room above the detached garage. Did not have our own refrigerator so we had to take our stuff up and down to the main house through the alley. Also did not have an air conditioner that worked in it not very hot up there. Our situation was not great either.

2/10

Poor

16 Mar 2026

Linda

The B&B website and other on-line links claims \"...excellent breakfast\" and \"the best breakfast in Annapolis\". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere.

Partner

8/10

Excellent

15 Mar 2026

Raymond

Excellent location.

Limited breakfast.

Partner

4/10

Poor

16 Feb 2026

Joseph

My prepaid $50.00 parking spot was not available. I was told to park in municipal lot. I refused and they made another arrangement for me to park.
No elevator. Had to carry luggage up and down 3 long steep flights of stairs. No mention about lack of elevators in promotion and listing materials.
No hot water in the morning (7:00) at the toilet room sink or in the shower despite running it for 30 minutes. No one on premises to assist. After returning from breakfast 2 hours later I was told the hot water was working. By this time I was packed, dressed and ready to depart. Too little too late.
Ceiling fan set on high and noisy with no way to slow it. Had to turn it off despite room being warm.
No one from management or otherwise available on premises to assist.
Would not recommend. Keep in mind I paid $400.00 one night for two adults. So many better options available in Annapolis.

Leisure Partner

6/10

Pleasant

16 Dec 2025

shawn

The stay was fine, I paid Expedia and then was told by the property that I didnt pay, even after I showed them a receipt. Then they tried to charge my credit card for next several months, even after we spoke and they weren’t authorized to charge my card, they need to resolve their issues with Expedia. This has never happened to me before, and I travel a lot.

Business

10/10

Exceptional

14 Nov 2025

Elizabeth

The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again.

6/10

Pleasant

03 Nov 2025

Kathy

Overpriced for what it offered. $500+ for a single night at the property sans breakfast or parking. Room itself was small with no real historic flair or charm. Found a used washcloth on the floor housekeeping had overlooked. To check in during peak hours we had to call hotel staff (attending to other properties when we arrived) in order to get access to the room. If this property were about $200 less expensive, I would have zero complaints, but to spend that amount of money I expected way more.

10/10

Exceptional

30 Jul 2025

Martha

In town treasure!

This B&B is in such a perfect location! Easily walkable to all the things we wanted to do. Staff was immediately attentive and there for your every need. Rooms were wel appointed but a bit on the small side. Living room and front porch were wonderful places to relax and take in the sights or just chill on the porch swing. Breakfast choices were all delicious and graciously served. Only drawback was parking was pretty pricey for the small lot. Definitely reccommend!

Partner

10/10

Exceptional

17 Jul 2025

Linda

Lovely B&B close to EVERYTHING!
The host were so kind and helpful.
The common areas were very nice as well as the front porch!

6/10

Pleasant

11 Jul 2025

Anne

Delicious breakfast. Utilitarian room- perfectly acceptable but we expected a higher level given price point.

Leisure Partner

10/10

Exceptional

09 Apr 2025

Hubert

Wonderfully friendly staff, great location, and beautiful property

Leisure Partner

10/10

Exceptional

30 Jan 2025

Paul

Great breakfast

Comfortable stay, high quality amazing service. Within walking distance to everything

Business Self

10/10

Exceptional

11 Jan 2025

Sandra

Great location right across from the Naval Academy and restaurants in Annapolis. Friendly and attentive owners and staff.

10/10

Exceptional

14 Dec 2024

Patricia

Easy check in, nice accommodations.

Leisure Partner

2/10

Poor

12 Nov 2024

Jennifer

The advertisement through Expedia is misleading, it states Bed & breakfast, free breakfast included. I paid for the stay in full only to see a charge on my card after the guest checked out, no bill was sent, when called they said it was for the breakfast; this is totally unacceptable. I would not recommend this hotel to anyone.

10/10

Exceptional

21 Sep 2024

Joseph

Very nice facility. Close to shops and restaurants.

Leisure Partner

10/10

Exceptional

25 Aug 2024

Dennis

Great place great people

8/10

Excellent

10 Jul 2024

Jonathan

The room over the garage was just ok

10/10

Exceptional

16 Jun 2024

Kevin

Great place to stay when visiting Annapolis.

Leisure Family

10/10

Exceptional

07 Jun 2024

Richard

Excellent

Excellent staff. Excellent room. Excellent breakfast. Fantastic location! Spent some lovely time on the front porch.

Partner

4/10

Poor

02 Jun 2024

Verified traveler

Remarkably underwhelming

We were baffled by other reviews of this inn, as well as the price (several hundred dollars per night for what was the least comfortable stay of our trip). We stayed in the Loft room (maybe that was the problem?), which is a room over the detached garage behind the house. The room smelled strongly of industrial cleaning products, had lime green duct tape to highlight steps around the room, and was generally underwhelming. The window had slatted blinds that didn’t block out the light, even at night, when a line of light from the house floodlights fell directly across the pillow, making it impossible to sleep. Also, perhaps the bedding in the other rooms was nicer, but ours clearly wasn’t Frette (see photo).

Breakfast was the quality of a basic chain hotel and though the setting was much nicer, there were no clean utensils or tables. Staff was absent to request help from.

The $50 “valet parking” is parking behind the house, by the door to the Loft.

Overall we found the stay disappointing, particularly given the price point. The location for those going to the Naval Academy is great, so perhaps if that’s your need and you stay in a different room, it will be good enough. For us, it was not.

8/10

Excellent

26 May 2024

Cecily

Paying for location

You’re paying for the location, which is excellent. Debo was extremely helpful. Could have had more thorough instructions on internet, front door. Housekeeping could have been better. Chesapeake 1 room was quiet, but extremely small with the tiniest bathroom possible. I would ask for a larger room if available.

Friends_and_family Family

10/10

Exceptional

06 Apr 2024

Beth

Very close to downtown!

Leisure Partner

2/10

Poor

25 Jul 2023

Dale

First and foremost, the property photos are not as advertised on the website. The common areas are nice, but the room accommodations were terrible, and the service was extremely poor. We were placed in a room behind the dining room which was down a hallway next to the kitchen across from the washer/dryer next to where the trash was kept each day. Furthermore, the photos on the website don’t show a room that looks anything like ours and when we inquired with the one and only staff person on-site, we were told our room isn’t listed on the site photos. This is misleading for a small inn to not show all the rooms available, particularly leaving off the less desirable ones. When we tried to get moved to a new room (as they weren’t sold out according to their misleading website) we were told we’d have to pay an extra $100 per night to move (we were already paying nearly $400 a night so that was simply unacceptable).
As we were next to the kitchen, it was noisy every morning and so much so that they gave us a white noise to help block the noise, which leads us to believe that this is an ongoing issue that others have complained about.
To be quite honest, we were confused why this was even a room they would rent out as there is no way anyone would stay in this room and have a good stay; we are confident that we can’t be the first people to have complained about this room. Strongly recommend booking elsewhere given the steep price.

Leisure Partner

10/10

Exceptional

16 Jun 2023

Michael

Great place for a weekend getaway in Annapolis. Quiet and walkable to all that Annapolis has to offer.

10/10

Exceptional

12 Apr 2023

Stephen

Very centrally located. VIP service throughout. Amazing breakfast. Lovely common areas.

Leisure Partner

10/10

Exceptional

08 Apr 2023

Andrea

The breakfast is a 10
The location is a 10
The hospitality is a 12
Highly recommended

Leisure Partner

8/10

Excellent

21 Mar 2023

Jan

Great place great location !!!
Worth your money!

Business

10/10

Exceptional

16 Mar 2023

Jason

Excellent service all around.

Leisure Family

10/10

Exceptional

04 Oct 2022

Robert

There was great communication before our visit and as we made our way to The Flag House Inn. We were greeted at our car, and helped with our luggage to our third floor room. The room was fine, with two small bathrooms - one with a toilet and sink, and one had a shower and sink. The property had recently changed ownership, so the staff was new and the property was being renovated. This was not a problem for us, and we had a pleasant stay. Breakfast was great, and the cook/server was very friendly. The B&B is right across the street from the visitor entrance to the naval academy. It was an easy walk to everything we wanted to see and do in Annapolis and Eastport. Parking was a little tight behind the building, but they parked our car for us and we didn't need it again until we left.

Leisure Partner

10/10

Exceptional

15 Sep 2022

Patricia

We were very shocked when we arrived that the inn was under renovations. We were not told of this when we booked. The smell of paint and dust everywhere. We felt that we were inconveniencing the contractors if we had to go up or down the steps. Also all of the staircases were covered in tarp which would be dangerous for someone coming down the steps. Also your website is very deceiving. Everything we read and the pictures we saw about the inn related too the previous owners. Again it was deceiving. Website is not updated. With other B&B’s that we used in the past they all had complimentary snacks throughout the day. For example cheese and crackers or cookies and sometimes tea time. All that was complimentary was coffee and a pitcher of water. Finally, we had too ask for extra bath towels.

Partner

10/10

Exceptional

04 Jun 2022

Maryalice

This property was very clean and the hosts were superb.
Breakfasts were out of this world! Very safe location and close to everything. Free off street parking as well! Highly recommend.

Leisure Self

10/10

Exceptional

21 Mar 2022

Charles

Warm, friendly, hospitable attitude of Owners. Detail oriented, they could not possibly have done more to make our getaway (and wife’s Birthday) a more pleasant one. It was quite obvious that they sincerely cared about our satisfaction with them, the Inn, and our entire weekend. We recommend highly anyone considering staying there to do so.

Leisure Family

10/10

Exceptional

27 Sep 2021

kELLEY

Stay here you won't be sorry

We had a great stay with very friendly customer service. Easy check in and out. Comfortable room and clean. Historic and we loved that with walking distance to everything. Free Wifi and parking were awesome with a homemade breakfast included. All great.

Partner

10/10

Exceptional

04 Jul 2021

Verified traveler

Excellent communication in advance of our arrival made planning easy.

Leisure Family

10/10

Exceptional

12 Apr 2021

Verified traveler

It is located in a great area and it is very relaxed. Marty and Carmel were very nice and helpful.

Leisure Partner

10/10

Exceptional

08 Mar 2021

Verified traveler

This b&b in Annapolis is just Perfect! Carmel and Marty are wonderful hosts, know the best restaurants in town, and their breakfast is delicious! (Marty even shared some recipes with us).
Our room was beautiful, comfortable, warm, spacious and very clean with high Covid awareness. Location couldn’t be better! Just few steps from Main st, yet quiet. I highly recommend this place!

Leisure Partner

10/10

Exceptional

22 Feb 2021

Verified traveler

Flag House Inn is awesome. Marty and Carmel were great hosts. Food was phenomenal! Presentation, quality and quantity was perfect. Great location. Accommodations were top notch. Great care taken with regard to Covid. Would highly recommended and will return there.

Leisure Family

10/10

Exceptional

18 Aug 2020

Paola

We truly enjoyed our time at the Flag House Inn; our home away from home. Marty and Carmel were so friendly and very accomodating. Even with the Pandemic, I never felt unsafe here. The room was super clean and I am very appreciative of the precautions they took during our stay there. We will definitely be staying here again!

Leisure Partner

10/10

Exceptional

04 Jul 2020

Andrea

Spectacular stay

Everything about the stay was spectacular: the welcome, the cleanliness, the location, the breakfast. Thank you!

Partner

10/10

Exceptional

03 Jul 2020

Dennis

My wife and I celebrated our 25 wedding anniversary while staying at the Flag House Inn. It was a wonderful experience. The room was recently updated, so it was very clean and modern. They are doing a great job dealing with the covid issue. The breakfast was fantastic and if you say nice thing to the host you may get an extra cinnamon roll!!! Carmel and Marty were wonderful hosts and spot on with their suggestions on where to eat and sight-see in town. They even fly your flag on the porch from the state or country you are coming from, it's these small details that really set this place apart. The location is perfect, you are literally across the street from the entrance to the Academy and a block from all the restaurants and water. Thank you for a memorable 25th anniversary!!! We look forward to coming back soon!!!

Partner

10/10

Exceptional

02 Jun 2020

Verified traveler

Beautiful area and our first time in a bed and breakfast which we really enjoyed! Clean and they were very good at keeping up with sanitizing everything with the covid virus. Food was wonderful and they had great suggestions of where to go to eat and what to do. Definitely would recommend to others!

Partner

10/10

Exceptional

02 Jan 2020

Jonathan

Great all around

Great location across from the Naval Academy with walking distance to all of Historic Annapolis. The owners were very helpful and made an amazing breakfast for us. Historic building with all the needed modern amenities. Truly a special place we hope to visit again!

Partner

10/10

Exceptional

29 Dec 2019

Pam

Breakfast was wonderful. Very unique and delicious. Hosts were very helpful with advice about seeing Annapolis. Other guests very friendly. Excellent conversation around the breakfast table. Location is outstanding, just steps from shops and restaurants and literally across the street from USNA. We would return. Highest recommendation

Leisure Partner

10/10

Exceptional

02 Oct 2019

Verified traveler

The individualized experience and the warm attention

Leisure Self

10/10

Exceptional

22 Sep 2019

Verified traveler

Visiting my son Tim, who lives very near by. Room was beautifully appointed and comfy. Bathroom was lovely with very high quality linens and soaps. Breakfast was hearty and beautifully presented- a delightful surprise. Owners, and other guests, were friendly.

Friends_and_family Family