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Flag House Inn

3.5 star property

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Photo gallery for Flag House Inn

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.
A dark blue bookshelf with decorative items and books.
A neatly made bed with white bedding, a striped pillow, and a vase with white flowers on a bedside table.
A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.
Point of interest

Reviews

9.2 out of 10
Wonderful

Popular amenities

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

Explore the area

View in a map
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

A bedroom with a bed, a chair, a dresser, and a window.

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

A bedroom with a bed, a dresser, a chair, a TV, and framed pictures on the walls.

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

A bedroom with a large bed, a bench, two bedside tables, and a window with a view.

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

A bedroom with a bed, bedside tables, a bench, and artwork on the walls.

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
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  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
4.5 out of 5, Wonderful, 1,880 reviews
The price is €125
includes taxes & fees
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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.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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

Tyler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Nathan

Liked: Cleanliness, amenities, property conditions & facilities
Great location. Beautiful room and exemplary service.
Stayed 1 night in Mar 2026
Verified

8/10 Good

Raymond

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent location. Limited breakfast.
Stayed 1 night in Mar 2026
Verified

8/10 Good

Lorraine

Liked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 1 night in Apr 2026
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

Hubert

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

2/10 Terrible

Linda

Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
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.
Stayed 3 nights in Mar 2026
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

Patricia

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

2/10 Terrible

Richard

Disliked: Property conditions & facilities
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.
Stayed 1 night in Mar 2026
Verified

6/10 Okay

Demetrios

Liked: Cleanliness, staff & service
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.
Stayed 1 night in Mar 2026
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

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

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

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

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

Jason

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

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

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