Flag House Inn

Bed & breakfast with free breakfast, steps from U.S. Naval Academy

Choose dates to view prices

Where to?

Dates

August 2025

September 2025

Stunning two-story home with a charming porch and symmetrical facade, featuring a central entrance and evenly spaced windows.

Cozy retreat with a large bed, bedside table, and a beautiful botanical print.

Enjoy a view of the historic cityscape from the comfort of this stylish room, featuring a large window and flat-screen TV.

Enjoy meals with family and friends at this spacious dining table, surrounded by comfortable chairs and a warm fireplace.

Cozy seating area with a fireplace and leather armchairs.

Overview
Rooms
Location
Policies

Exceptional

Popular amenities

Parking available
Housekeeping
Air conditioning
Free WiFi
Business services

Explore the area

26 Randall St, Annapolis, MD, 21401

U.S. Naval Academy
‪1 min walk‬
Annapolis City Dock
‪2 min walk‬
Navy-Marine Corps Memorial Stadium
‪3 min drive‬
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
‪34 min drive‬

Room options

Cozy retreat with a large bed, bedside table, and cushioned bench.

Fleet Suite

400 sq ft
City view
Sleeps 4
1 King Bed and 2 Twin Beds

Sailing Capital Room

250 sq ft
Sleeps 2
1 Double Bed

Relax in this serene bedroom with a large bed, flat-screen TV, and comfortable armchair.

Chesapeake Suite

205 sq ft
City view
Sleeps 2
1 King Bed

Classic bedroom with a large bed, bedside tables, and a comfortable bench.

Commodore Suite

Exceptional

City view
Sleeps 2
1 King Bed

Relax in a stylish room with a neatly made bed, a comfortable armchair, and a rustic wooden ceiling.

Loft Suite

Exceptional

150 sq ft
Sleeps 2
1 Queen Bed

About the neighborhood

Annapolis

Located in Historic District, Flag House Inn is next to popular attractions like U.S. Naval Academy and Annapolis City Dock. Each of the 5 rooms at this 3.5-star bed & breakfast includes free minibar items, a sitting area, and an espresso maker.

View more B&B in Annapolis

What's nearby

U.S. Naval Academy - 1 min walk - 0.0 miles
Annapolis City Dock - 2 min walk - 0.1 miles
Maryland State House - 5 min walk - 0.3 miles
Navy-Marine Corps Memorial Stadium - 3 min drive - 1.6 miles
Chesapeake Bay Bridge - 14 min drive - 9.5 miles

Getting around

Odenton Station - 21 min drive
Fort Meade, MD (FME-Tipton) - 25 min drive

Restaurants

‪The Choptank - ‬3 min walk
‪Starbucks - ‬4 min walk
‪O'Brien's Annapolis' Original Steakhouse - ‬4 min walk
‪Chick & Ruth's Delly - ‬7 min walk
‪Mc Garvey's Saloon - ‬2 min walk

About this property

Flag House Inn

Bed & breakfast with free breakfast, steps from U.S. Naval Academy

Guests of Flag House Inn enjoy access to free WiFi in public areas, meeting rooms, and refrigerator in a common area. Valet parking is offered for USD 50 per night. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include free newspapers, a terrace, and a fireplace in the lobby.

55-inch LED TVs come with digital channels, and guests can stay connected with free WiFi. Bathrooms offer hair dryers and free toiletries, and memory foam beds with Frette Italian sheets ensure a restful night. Other amenities include free minibar items, sitting areas, and espresso makers.

Languages

English

Similar properties

Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Pet friendly
Free WiFi
Air conditioning
Gym

$143 nightly

Aug 17 - Aug 18

Total includes taxes and fees

Property amenities

Internet

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

Parking and transportation

Self parking on site (USD 50 per night; includes in/out privileges)
Valet parking on site (USD 50 per night; includes in/out privileges)

Food and drink

Free local cuisine breakfast available daily 8:30 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

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

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 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 available

Special check-in instructions

The front desk is open daily from 7:30 AM - 6:00 PM

Guests planning to arrive outside of 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

Access methods

Front desk (limited hours), key retrieval

Pets

Service animals exempt from fees

Children and extra beds

This property doesn't allow children 11 and younger (only guests older than 11 are allowed)

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

Deposit: USD 50.0 per stay

These are all of the charges provided to us by the property.

Optional extras

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

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

You need to know

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 without COVID-19 vaccination

Check-in: 4:00 PM—-8:00 PM
Check-out: 11 AM
Minimum check-in age: 21

The front desk is available during limited hours. Driving? This property offers parking (fees apply).

We should mention

Details about charges, deposits, or other important information:

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
This property accepts credit cards. Cash is not accepted.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.
Cashless payment methods are available for all transactions and masks are required in public areas for unvaccinated guests.

Additional information about polices, regulations, and more:

There are no elevators.
No rollaway or extra beds are available.
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

Frequently asked questions

What's there to do near Flag House Inn?

This bed & breakfast is situated in Historic District, just steps from Annapolis City Dock and William Paca House, and within a short walk of Ego Alley. You'll also find Maryland State House and Annapolis Harbor less than a mile away.

How much does it cost to stay at Flag House Inn?

As of Aug 11, 2025, prices found for a 1-night stay for 2 adults at Flag House Inn on Aug 12, 2025 start from $139.5, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is there parking available at Flag House Inn?

Yes, valet parking is offered for USD 50 per night with in/out privileges.

Does Flag House Inn have a casino on the premises?

No, Flag House Inn doesn't have a casino.

Will I find an indoor pool at Flag House Inn?

No, there is no indoor pool at this bed & breakfast.

What do couples enjoy most about Flag House Inn?

Amenities that appeal to couples at this bed u0026 breakfast include a memory foam mattress, a minibar stocked with free items, and an espresso maker.

Are there hot tubs at Flag House Inn?

No, this bed & breakfast doesn't have a spa tub.

Does Flag House Inn feature a restaurant that includes a breakfast menu?

Flag House Inn offers free breakfast (local cuisine) each morning though there is no restaurant.

Will Flag House Inn allow pets to stay free of charge?

No, pets aren't allowed at Flag House Inn though service animals are welcome.

Are there connecting rooms at Flag House Inn?

No, this bed & breakfast doesn't feature connecting guestrooms.

What is the closest airport to Flag House Inn?

The closest major airport to Flag House Inn is Fort Meade, MD (FME-Tipton), which is 21 mi away (25 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is located 25.2 mi away (30-minute drive).

Can I book a room with a balcony at Flag House Inn?

No, there aren't any guestrooms with balconies at Flag House Inn.

Flag House Inn Reviews

9.6

Exceptional

9.8/10

Cleanliness

9.8/10

Staff & service

9.8/10

Amenities

9.4/10

Property conditions & facilities

8.8/10

Eco-friendliness

10/10 Excellent

Hubert, Macon

Traveled with partner

Apr 10, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Wonderfully friendly staff, great location, and beautiful property

Stayed 1 night in Apr 2025

10/10 Excellent

Paul

Business traveler

Jan 30, 2025

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

10/10 Excellent

Elizabeth

Jan 12, 2025

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

Stayed 1 night in Jan 2025

10/10 Excellent

Sandra

Jan 11, 2025

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

2/10 Terrible

Prashant

Dec 15, 2024

Disliked: Property conditions & facilities, room comfort

Stayed 1 night in Dec 2024

10/10 Excellent

Patricia

Traveled with partner

Dec 15, 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Easy check in, nice accommodations.

Stayed 1 night in Dec 2024

8/10 Good

Calista

Dec 9, 2024

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

Stayed 2 nights in Dec 2024

10/10 Excellent

Deangello

Nov 25, 2024

Stayed 2 nights in Nov 2024

2/10 Terrible

Jennifer

Nov 12, 2024

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

10/10 Excellent

Shelley

Nov 12, 2024

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

Stayed 2 nights in Nov 2024

10/10 Excellent

Katja

Nov 8, 2024

Stayed 1 night in Nov 2024

10/10 Excellent

Caitlin

Oct 18, 2024

Stayed 1 night in Oct 2024

10/10 Excellent

Brookelyn

Sep 22, 2024

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

Stayed 1 night in Sep 2024

10/10 Excellent

Joseph

Traveled with partner

Sep 21, 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Very nice facility. Close to shops and restaurants.

Stayed 1 night in Sep 2024

10/10 Excellent

Dennis

Aug 25, 2024

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

Great place great people

Stayed 1 night in Aug 2024

6/10 Okay

Catherine

Jul 28, 2024

Liked: Cleanliness, property conditions & facilities, room comfort

Disliked: Staff & service

Stayed 1 night in Jul 2024

8/10 Good

Jonathan, Dulles

Jul 10, 2024

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

The room over the garage was just ok

Stayed 1 night in Jul 2024

10/10 Excellent

Kevin

Traveled with family

Jun 17, 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great place to stay when visiting Annapolis.

Stayed 1 night in Jun 2024

10/10 Excellent

Richard

Jun 8, 2024

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

8/10 Good

Cecily

Traveled with family

May 26, 2024

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

10/10 Excellent

Beth

Traveled with partner

Apr 7, 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Very close to downtown!

Stayed 1 night in Apr 2024

10/10 Excellent

Verified traveler

Sep 18, 2023

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

Stayed 1 night in Sep 2023

10/10 Excellent

Gregory

Aug 23, 2023

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

Stayed 1 night in Aug 2023

2/10 Terrible

Dale

Traveled with partner

Jul 25, 2023

Disliked: Cleanliness, staff & service, property conditions & facilities

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.