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.
Payments made by partners impact the order of prices displayed. Room types may vary.
The listings of booking offers for each property take into account the compensation paid to us by our partners. Prices shown may be for varying room types. Prices displayed are the lowest available, corresponding to the least expensive room type available, as provided from our partners as of the time of the user’s search.

Flag House Inn

avatar-imageavatar-imageavatar-image
Traveller (170)
Room & Suite (34)
Dining (29)
What is Travellers’ Choice?
Tripadvisor gives a Travellers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.

View prices for your travel dates

Prices are provided by our partners, and reflect total costs of the stay, including all taxes and fees known to our partners. Please see our partners for more details.

About

#1 of 15 B&Bs in Annapolis
Location
Cleanliness
Service
Value
Travellers' Choice
GreenLeaders Bronze level
The Flag House Inn is where classic style meets historic locality. The U.S. Naval Academy is located steps outside our front door, along with award-winning Annapolis restaurants and charming boutiques that line the brick sidewalks of Historic Annapolis. Come experience the comfortably refined sophistication of this intimately sized and design-driven Annapolis icon.
Read more
Suggest edits to improve what we show.Improve this listing
Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Canoeing offsite
Walking tours
Taxi service
Baggage storage
Newspaper
Parking
Wifi
Special diet menus
Board games / puzzles
Non-smoking hotel
Outdoor furniture
Shared lounge / TV area
First aid kit
Umbrella
Private check-in / check-out
Show more
Room features
Allergy-free room
Air purifier
Air conditioning
Desk
Housekeeping
Seating area
Cable / satellite TV
Bath / shower
Sofa
Wardrobe / wardrobe
Bottled water
Private bathrooms
Wake-up service / alarm clock
Flatscreen TV
Complimentary toiletries
Hair dryer
Show more
Room types
City view
Landmark view
Non-smoking rooms
Suites
Family rooms
Good to know
HOTEL STYLE
Green
Historic Hotel
Languages Spoken
English
887Reviews3Q+A100Room tips

Reviews
We perform checks on reviews.
Tripadvisor’s approach to reviews
Before posting, each Tripadvisor review goes through an automated tracking system, which collects information, answering the following questions: how, what, where and when. If the system detects something that potentially contradicts our community guidelines, the review is not published.
When the system detects a problem, a review may be automatically rejected, sent to the reviewer for validation, or manually reviewed by our team of content specialists, who work 24/7 to maintain the quality of the reviews on our site.
Our team checks each review posted on the site disputed by our community as not meeting our community guidelines.
Learn more about our review moderation.

Traveller rating
  • 830
  • 40
  • 7
  • 3
  • 7
Time of year
Traveller type
Language
  • More
Selected filters
  • Filter
  • English
Popular mentions
Sort by:
Most Recent
avatar-image
Elizabeth W wrote a review Oct 2022
2 contributions
We enjoyed a fabulously comfortable stay with attentive hosts, and a delicious homemade breakfast every day. The property has been beautifully decorated, our bed was amazingly luxurious. Many thanks, Clint, Cody, Debbie and Phillipa.
Read more
Date of stay: October 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Richard R wrote a review Oct 2022
1 contribution
Our four day stay in Annapolis was just terrific thanks to Flag House Inn and its great team (Clint, Cody & Debbie -- wonderful, thoughtful hosts). Quick stroll to downtown or the Naval Academy main gate, super convenient on-site parking, spacious rooms, great breakfast and more! We visit Annapolis a lot....we only wish we had discovered Flag House Inn sooner!
Read more
Date of stay: October 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Bob M wrote a review Oct 2022
Landenberg, Pennsylvania75 contributions72 helpful votes
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
Read more
Date of stay: September 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Mike L wrote a review Sept 2022
Columbus, Ohio, United States4 contributions5 helpful votes
My wife and I spent a couple nights in Annapolis at the Flag House Inn. First, the location is perfect for exploring the historic downtown and harbor area of Annapolis. Just a quick walk (a couple blocks) and you’re in the heart of it all. Next, the Inn is beautiful and well managed. The innkeepers are always responsive and there to serve without hovering. A chef prepared breakfast each morning is offered, ours were delicious! The Inn also offers free, off street parking, which is rare in the area. The rooms have recently been redecorated and are modern, stylish and comfortable. If you are headed to Annapolis I highly recommend the Flag House Inn!
Read more
Date of stay: September 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
dge74 wrote a review Sept 2022
Langhorne, Pennsylvania35 contributions11 helpful votes
Great time, great place. The new owners really made sure we felt comfortable. You can tell they want to make sure the Inn remains at the top of the Trip Advisor rankings. Our room (The Chesapeake) was beautiful. Breakfast every morning was delicious.
Read more
Date of stay: September 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Scott W wrote a review Sept 2022
Bristol, Rhode Island6 contributions5 helpful votes
We stayed at the Flag House Inn in September of 2022, shortly after the new ownership group took over, and this property is a gem! They have updated the previously out-of-style furnishings with tasteful options that are still classic in style. The professionalism exhibited by the staff is world-class. I cannot wait to visit the Flag House Inn again very soon!
Read more
Date of stay: September 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
1 Helpful vote
Helpful
Share
avatar-image
Footprints71473 wrote a review Sept 2022
1 contribution
Apparently the property changed hands and the web page was not updated. We booked based on reviews of the previous owners. When we arrived, the property was undergoing some construction , the former owners were gone and the room was stark and uninviting. No bedside tables, no phone and no clock. NO local TV channels. 2 chairs and a lamp plus the bed. False advertising as a recent check of the webpage still showed the old rooms/images. Unfortunately had to leave 1 day early due to family emergency- no breakfast was available ( table was set but no food anywhere). Would not refund any amount- gave us a credit but we wont go back. Very disappointing as this was our anniversary weekend. Hotel did not respond to email about the false advertising/conditions
Read more
Date of stay: August 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Carolina_Traveler_7 wrote a review Sept 2022
Charlotte132 contributions89 helpful votes
Difficult to rate this lodging. The new owners are trying to turn it into a luxury hotel. Everything that made it a traditional bed and breakfast is gone. But if you want an upscale, predictable room in a good location, this may be fine for you. What is gone: fabulous breakfasts, baked goods, people who know the area, local owner collections of the area ( library, art and decor local to the area) , regular TV. What is new: a serviceable breakfast (the cook is very nice, and it’s certainly better than the chain hotels); fashionable black/off white anonymous furniture, you tube tv only (spotty internet when we were trying to stream our programs; we eventually gave up), multiple friendly guys in suits who carry your luggage upstairs. They are trying the “upscale mode where
Read more
Date of stay: August 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
avatar-image
Rob D wrote a review Aug 2022
2 contributions
We recently stayed at the Flag House Inn in Annapolis, MD. The B&B was located in an excellent location close to water activities, restaurants, and bars. The staff was outstanding and went out of their way to ensure we had all that we needed during our stay. I would highly recommend this B&B for anyone wanting to stay in Annapolis.
Read more
Date of stay: August 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
Response from Debbie Ramsden, General Manager at Flag House Inn
Responded 26 Aug 2022
Thank you for your spectacular review! The pleasure was all ours. Hosting you in Annapolis was a treat for our staff, and we look forward to welcoming you back for another memorable stay.
Read more
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
avatar-image
sailing1249 wrote a review Jul 2022
Glen Burnie, Maryland10 contributions4 helpful votes
The inn was exceptional! We loved the location, accommodations, and the delicious breakfast! The owners were wonderful and really made our stay special. It is in the heart of Annapolis and a short walk to everything. I highly recommend it!
Read more
Date of stay: July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
Share
Response from Debbie Ramsden, General Manager at Flag House Inn
Responded 11 Aug 2022
Thank you so much for the terrific review! We enjoyed welcoming you to this special property, and I hope to see you again very soon. Sincerely, Debbie R. General Manager
Read more
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Not the right property for you?
There are more places to choose from in the Annapolis area.
PRICE RANGE
$399 - $560 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
flag house hotel annapolis
LOCATION
United StatesMarylandAnnapolis
NUMBER OF ROOMS
6
Prices are provided by our partners, and reflect total costs of the stay, including all taxes and fees known to our partners. Please see our partners for more details.
Is This Your Tripadvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

FLAG HOUSE INN - B&B Reviews & Price Comparison (Annapolis, MD) - Tripadvisor