Flag House Inn

City-center B&B, steps from Annapolis City Dock

Choose dates to view prices

Sun, Apr 19
Mon, Apr 20
April 2026
5
May 2026
In the heart of Annapolis, Flag House Inn offers a warm welcome with local breakfast and free in-room WiFi. Unwind by the lobby fireplace or take in city views from the charming terrace. With valet parking and tour assistance, this historic bed & breakfast has left a lasting impression on previous guests.
Wonderful

Popular amenities

  • Parking available
  • Free WiFi
  • Air conditioning

Main amenities (11)

  • Daily housekeeping
  • Valet parking
  • Self parking
  • Meeting rooms
  • Terrace
  • Lobby fireplace
  • Refrigerator in a common area
  • Concierge services
  • Free newspapers in the lobby
  • Limited hour front desk
  • Tour/ticket assistance

Feel at home (6)

  • Private bathroom
  • Separate sitting area
  • Television
  • Terrace
  • Daily housekeeping
  • Coffee/tea maker
$174 nightly
$199 total
Apr 7 - Apr 8
Total with taxes and fees

Room options

Showing 5 of 5 rooms

Sailing Capital Room

  • 250 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
Loft Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Loft Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Loft Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Loft Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Loft Suite

Exceptional
  • 150 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Chesapeake Suite

Very good
  • City view
  • 205 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
Commodore Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Commodore Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Commodore Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Commodore Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Commodore Suite

Exceptional
  • City view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
Fleet Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Fleet Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Fleet Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Fleet Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Fleet Suite

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

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About the neighborhood

Map
26 Randall St, Annapolis, MD, 21401

What's nearby

  • U.S. Naval Academy - 1 min walk - 0.1 km
  • Annapolis City Dock - 2 min walk - 0.2 km
  • William Paca House - 2 min walk - 0.2 km
  • Hammond-Harwood House - 3 min walk - 0.3 km
  • Maryland State House - 5 min walk - 0.4 km

Getting around

  • Fort Meade, MD (FME-Tipton) - 25 min drive
  • Baltimore Washington Intl. Airport (BWI) - 30 min drive
  • College Park, MD (CGS) - 34 min drive
  • Baltimore, MD (MTN-Martin State) - 50 min drive
  • Easton, MD (ESN-Easton - Newnam) - 51 min drive
  • Odenton Station - 21 min drive
  • Bowie State Station - 25 min drive
  • Baltimore-Washington International Airport Station - 31 min drive

Restaurants

  • ‪The Choptank - ‬3 min walk
  • ‪Starbucks - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬3 min walk
  • ‪Buddy's Crabs & Ribs - ‬3 min walk
  • ‪Annapolis Market House - ‬2 min walk

About this property

Flag House Inn

Flag House Inn offers a fantastic location, putting you just a 5-minute walk from U.S. Naval Academy and Annapolis City Dock. Free perks include WiFi and continental breakfast daily between 8:00 AM and 10:00 AM. Also, Maryland State House and Navy-Marine Corps Memorial Stadium are just a 5-minute drive away.

At a glance

Hotel size

    • 5 rooms

Arriving/Leaving

    • Check-in start time: 4:00 PM; Check-in end time: 8:00 PM
    • Contactless check-in available
    • Early check-in subject to availability
    • Minimum check-in age: 21
    • Check-out time is 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
    • Information provided by the property may be translated using automated translation tools

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21

Children

    • Children (11 years old and younger) not allowed

Pets

    • Pets not allowed
    • Service animals welcome

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms

Parking

    • Onsite self parking (USD 50 per night; includes in/out privileges)
    • Onsite valet parking (USD 50 per night; includes in/out privileges)

Other information

    • Designated smoking areas

Property amenities

Food and drink

  • Free continental breakfast each morning 8:00 AM–10:00 AM
  • Shared refrigerator

Working away

  • Meeting rooms

Services

  • Front desk (limited hours)
  • Concierge services
  • Tour/ticket assistance
  • Free newspapers in lobby

Facilities

  • Terrace
  • Fireplace in lobby

Accessibility

  • Handrails in hallways
  • Handrails in stairways
  • Closed captioned TV
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Thin carpet in room

Room amenities

Be entertained

  • 55-inch LED TV
  • Digital TV channels

Home comfort

  • Climate-controlled air conditioning and heating
  • Ceiling fan
  • Free stocked minibar
  • Espresso maker
  • Iron/ironing board (on request)
  • Window screens

Sleep well

  • Hypo-allergenic bedding
  • Premium bedding
  • Memory foam mattress

What to enjoy

  • Individually furnished and decorated
  • Separate sitting area

Freshen up

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

Stay connected

  • Free newspapers
  • Free WiFi
  • Electrical adapters/chargers

Food and drink

  • Free bottled water

More

  • Daily housekeeping
  • Guidebooks/recommendations
  • Restaurant dining guide

Fees & policies

Refundable deposits

  • Deposit: USD 50.0 per stay

Optional extras

  • Early check-in can be arranged for an extra charge of USD 95 (subject to availability)
  • Late check-in between 11:00 AM and 1:00 PM can be arranged for an extra charge of USD 95

Parking

  • Self parking costs USD 50 per night with in/out privileges
  • Valet parking costs USD 50 per night with in/out privileges

Policies

This property does not have elevators.
Guests can rest easy knowing there's a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit on site.
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover
Cashless transactions are available.
Masks are required in public areas for unvaccinated guests.

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

Are pets allowed at Flag House Inn?

Sorry, pets aren't allowed, but service animals are welcome.

Is parking offered on site at Flag House Inn?

Yes. Self parking costs USD 50 per night. Valet parking costs USD 50 per night.

What are the check-in and check-out times at Flag House Inn?

Check-in start time: 4:00 PM; Check-in end time: 8:00 PM. There's a charge of USD 95 for early check-in (subject to availability). Check-out time is 11 AM. Contactless check-in and check-out are available.

What is there to do at Flag House Inn and nearby?

Recommended spots to visit include U.S. Naval Academy (1-min walk) and Annapolis City Dock (1-min walk), along with Maryland State House (6-min walk) and Navy-Marine Corps Memorial Stadium (1.3 mi).

What's the area around Flag House Inn like?

Flag House Inn is in Historic District, a short 1-minute walk from U.S. Naval Academy and 3 minutes' walk from William Paca House.

Have a question?

Get instant answers with AI powered search of property information and reviews.

Flag House Inn Reviews

9.2

Wonderful

9.6

Cleanliness

10

Location

9.6

Staff & service

9.2

Property conditions & facilities

What guests liked

  • Breakfast was consistently described as great, delicious, and out of this world. (7 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Popular mentions

BreakfastParkingLocationRoom
Verified

6/10 Good

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.
Demetrios, 1-night trip
Verified

10/10 Exceptional

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.
Elizabeth, 1-night trip
Verified

10/10 Exceptional

Wonderfully friendly staff, great location, and beautiful property
Hubert, 1-night trip
Verified

10/10 Exceptional

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!
Linda, 2-night trip
Verified

10/10 Exceptional

Great place to stay when visiting Annapolis.
Kevin, 1-night trip
Verified

10/10 Exceptional

Easy check in, nice accommodations.
Patricia, 1-night trip
Verified

6/10 Good

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.
shawn, 1-night trip
Verified

10/10 Exceptional

Great location right across from the Naval Academy and restaurants in Annapolis. Friendly and attentive owners and staff.
Sandra, 1-night trip
Verified

10/10 Exceptional

Great breakfast

Comfortable stay, high quality amazing service. Within walking distance to everything
Paul, 1-night trip
Verified

10/10 Exceptional

The breakfast is a 10 The location is a 10 The hospitality is a 12 Highly recommended
Andrea, 3-night trip
Verified

10/10 Exceptional

Great place great people
Dennis, 1-night trip
Verified

10/10 Exceptional

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!
Martha, 2-night trip
Verified

10/10 Exceptional

Very nice facility. Close to shops and restaurants.
Joseph, 1-night trip
Verified

6/10 Good

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.
Kathy, 1-night trip
Verified

6/10 Good

Delicious breakfast. Utilitarian room- perfectly acceptable but we expected a higher level given price point.
Anne, 1-night trip
Verified

10/10 Exceptional

Great place for a weekend getaway in Annapolis. Quiet and walkable to all that Annapolis has to offer.
Michael, 2-night trip
Verified

10/10 Exceptional

Very close to downtown!
Beth, 1-night trip
Verified

10/10 Exceptional

Excellent

Excellent staff. Excellent room. Excellent breakfast. Fantastic location! Spent some lovely time on the front porch.
Richard, 1-night trip
Verified

10/10 Exceptional

Excellent service all around.
Jason, 1-night trip
Verified

10/10 Exceptional

Very centrally located. VIP service throughout. Amazing breakfast. Lovely common areas.
Stephen, 1-night trip
Verified

8/10 Very good

The room over the garage was just ok
Jonathan, 1-night trip
Verified

10/10 Exceptional

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!
Norm&Linda, 1-night trip
Verified

2/10 Poor

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.
Jennifer, 1-night trip
Verified

8/10 Very good

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.
Cecily, 4-night trip
Verified

10/10 Exceptional

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.
Robert, 2-night trip