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Flag House Inn

3.5 star property

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Photo gallery for Flag House Inn

Lobby lounge
Point of interest
Dining room
Lobby lounge
Chesapeake Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free Wi-Fi
  • Air-conditioning
  • Parking available
  • Business services
  • Housekeeping

Explore the area

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26 Randall St, Annapolis, MD, 21401
  • Place, U.S. Naval Academy
    ‪1 min walk‬
  • Place, Annapolis City Dock
    ‪2 min walk‬
  • Place, Maryland State House
    ‪5 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Room options

Sailing Capital Room

  • 23 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free Wi-Fi

View all photos for Loft Suite

Loft Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar

Loft Suite

10.0 out of 10
Exceptional
(1 review)
  • 14 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Chesapeake Suite

Chesapeake Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar

Chesapeake Suite

8.0 out of 10
Very good
(1 review)
  • City view
  • 19 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Commodore Suite

Commodore Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar

Commodore Suite

10.0 out of 10
Exceptional
(2 reviews)
  • City view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Fleet Suite

Fleet Suite | Frette Italian sheets, premium bedding, memory-foam beds, free minibar

Fleet Suite

  • City view
  • 37 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 2 Single Beds
  • Free Wi-Fi

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Meeting facility
Historic Inns of Annapolis
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  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
4.5 out of 5, Wonderful, 1,863 reviews
The price is CHF 121
includes taxes & fees
1 Jul - 2 Jul
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About this property

Flag House Inn

Valet parking, a fridge in a common area and concierge services are available at this bed & breakfast. Free continental breakfast and free WiFi in public areas are also provided. Additionally, self parking, free newspapers and tour/ticket assistance are on-site.
Flag House Inn offers 5 accommodations with free minibar items and espresso makers. This individually decorated and furnished accommodation has separate sitting areas. Memory foam beds feature Frette Italian sheets and premium bedding. 55-inch LED televisions come with digital channels.

Bathrooms include a shower, complimentary toiletries and hairdryers. Guests can surf the web using complimentary wireless Internet access. Additionally, rooms include free newspapers and complimentary bottles of water. Hypo-allergenic bedding and an iron/ironing board can be requested. Housekeeping is provided on a daily basis.

During your stay at Flag House Inn, you're just a quick walk from U.S. Naval Academy. Features include free breakfast and free WiFi in public areas, plus meeting rooms.
  • Free continental breakfast served daily
  • Free WiFi
  • Valet parking and self-parking available for a fee
  • Amenities include free newspapers in reception, meeting rooms and a terrace
  • Steps from U.S. Naval Academy and Annapolis City Dock
Free breakfast is available daily. Public spaces have free WiFi. A terrace, tour/ticket assistance, and concierge services are also featured at Flag House Inn. For a fee, parking is available.

Smoking is allowed in designated areas at this 3.5-star Annapolis bed & breakfast.

Guests are served a free continental breakfast daily from 8:00 AM to 10:00 AM.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transport

  • Parking on site (USD 50 per night; includes in/out privileges)
  • Valet parking on site (USD 50 per night; includes in/out privileges)
  • Limited on-site valet and self parking

Food and drink

  • Free continental breakfast available daily 8:00 AM to 10:00 AM

Conveniences

  • Free newspapers in lobby
  • Guidebooks
  • Limited-hour front desk
  • Shared refrigerator

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Tour and ticket assistance

Business services

  • Meeting rooms

Outdoors

  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Handrails in hallways
  • Handrails in stairways
  • Thin carpet in room
  • Upper floors accessible by stairs only
  • Well-lit path to entrance

More

  • Designated smoking areas
  • Fireplace in lobby

Room amenities

Bedroom

  • Frette Italian sheets
  • Hypo-allergenic bedding
  • Memory foam mattress

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Toothbrush and toothpaste (on request)
  • Towels provided

Entertainment

  • 55-inch LED TV with digital channels

Food and drink

  • Coffee/tea maker
  • Espresso maker
  • Free bottled water
  • Free stocked minibar
  • Restaurant dining guides

More

  • Air conditioning (climate-controlled)
  • Ceiling fan
  • Electrical adapters
  • Free daily newspapers
  • Heating (climate-controlled)
  • Individual decor
  • Individual furnishings
  • Iron/ironing board on request
  • Separate sitting area
  • Window screens

Policies

Check-in

Check-in start time: 4:00 PM; check-in end time: 8:00 PM
Early check-in subject to availability
Early check-in fee: USD 95
Contactless check-in and check-out are available
Late check-in fee: USD 95 for check-in between 11:00 AM and 1:00 PM
Minimum check-in age - 21

Check-out

Check-out before 11 AM
Contactless check-out

Special check-in instructions

The front desk is open daily from 7:30 AM - 6:00 PM
Guests planning to arrive outside normal check-in hours will receive an email within 48 hours before arrival with check-in instructions and key retrieval information; front desk staffed during limited hours
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
If you are planning to arrive after 7 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours), key retrieval

Pets

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children 11 and younger are not allowed at this property. All guests older than 11 are welcome.
  • Rollaway/extra beds are not available.

Payment types at the property

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • Deposit: USD 50.0 per stay

We've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Self-parking fee: USD 50 per night (in/out privileges)
  • Valet parking fee: USD 50 per night (in/out privileges)
  • Early check-in fee: USD 95 (subject to availability)
  • Late check-in fee: USD 95 for check-in between 11:00 AM and 1:00 PM

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit
Masks are required at the property for guests who have not received COVID-19 vaccination
The front desk at this property is open daily from 7:30 AM - 6:00 PM.
To arrange for check-in, guests must contact the property at least 24 hours prior to arrival using the information on the booking confirmation. Guests arriving after 7 PM must make advance arrangements by contacting the property using the information on the booking confirmation. Guests planning to arrive outside of normal check-in hours will receive an email with special check-in information and key retrieval information. Front desk staff will greet guests on arrival at the property.

We should mention

  • Children 11 years old and younger aren't allowed at this property.
  • This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).

Property is also known as

Flag House Inn Annapolis
Flag House Annapolis
Flag House Hotel Annapolis
Flag House Inn Annapolis
Flag House Inn Bed & breakfast
Flag House Inn Bed & breakfast Annapolis

Flag House Inn Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 75 out of 94 reviews
Rating 8 - Good. 7 out of 94 reviews
Rating 6 - Okay. 5 out of 94 reviews
Rating 4 - Poor. 2 out of 94 reviews
Rating 2 - Terrible. 5 out of 94 reviews

9.6/10

Cleanliness

9.6/10

Staff & service

9.4/10

Amenities

9.2/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Elizabeth

Liked: Cleanliness, amenities, property conditions & facilities
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.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Hubert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderfully friendly staff, great location, and beautiful property
Stayed 1 night in Apr 2025
Verified

10/10 Excellent

Kevin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay when visiting Annapolis.
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy check in, nice accommodations.
Stayed 1 night in Dec 2024
Verified

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, property conditions & facilities
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!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Sandra

Liked: Cleanliness, staff & service, property conditions & facilities
Great location right across from the Naval Academy and restaurants in Annapolis. Friendly and attentive owners and staff.
Stayed 1 night in Jan 2025
Verified

10/10 Excellent

Andrea

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The breakfast is a 10 The location is a 10 The hospitality is a 12 Highly recommended
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Dennis

Liked: Cleanliness, staff & service, property conditions & facilities
Great place great people
Stayed 1 night in Aug 2024
Verified

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great breakfast

Comfortable stay, high quality amazing service. Within walking distance to everything
Stayed 1 night in Jan 2025
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, property conditions & facilities
Great place for a weekend getaway in Annapolis. Quiet and walkable to all that Annapolis has to offer.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Joseph

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice facility. Close to shops and restaurants.
Stayed 1 night in Sep 2024
Verified

6/10 Okay

shawn

Disliked: Staff & service
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.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Beth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very close to downtown!
Stayed 1 night in Apr 2024
Verified

10/10 Excellent

Martha

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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!
Stayed 2 nights in Jul 2025
Verified

6/10 Okay

Anne

Liked: Staff & service
Delicious breakfast. Utilitarian room- perfectly acceptable but we expected a higher level given price point.
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Richard

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Excellent

Excellent staff. Excellent room. Excellent breakfast. Fantastic location! Spent some lovely time on the front porch.
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

Jason

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent service all around.
Stayed 1 night in Mar 2023
Verified

6/10 Okay

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.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Stephen

Liked: Staff & service, amenities, property conditions & facilities
Very centrally located. VIP service throughout. Amazing breakfast. Lovely common areas.
Stayed 1 night in Apr 2023
Verified

4/10 Poor

Joseph

Disliked: Amenities
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.
Stayed 1 night in Feb 2026
Verified

8/10 Good

Jonathan

Liked: Cleanliness, staff & service, property conditions & facilities
The room over the garage was just ok
Stayed 1 night in Jul 2024
Verified

10/10 Excellent

Norm&Linda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Friendly, interesting and knowledgeable hosts, excellent (and not unhealthy) breakfast, ideal location within three blocks of historic Annapolis and the U.S. Naval Academy. Early access to off-stret parking. It is a little expensive, but well worth it. We will stay again!
Stayed 1 night in Aug 2018
Verified

2/10 Terrible

Jennifer

Liked: Cleanliness, staff & service
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.
Stayed 1 night in Nov 2024
Verified

8/10 Good

Cecily

Liked: Staff & service, property conditions & facilities

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.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Robert

Liked: Staff & service, amenities
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.
Stayed 2 nights in Sep 2022