Flag House Inn

Property class: 3.5

Choose dates to view prices

Located close to Annapolis City Dock and Maryland State House, Flag House Inn provides free continental breakfast, a terrace, and a fireplace in the lobby. Stay connected with free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free WiFi
  • Air conditioning
  • Parking available
  • Business services
  • Housekeeping

Room options

Available filters for rooms
Showing 5 of 5 rooms

Sailing Capital Room

  • 250 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

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)
  • 150 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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
  • 205 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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
(3 reviews)
  • City view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Fleet Suite

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

Fleet Suite

10.0 out of 10
Exceptional
(1 review)
  • City view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 2 Twin Beds

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About the neighborhood

Located in Historic District, a neighborhood in Annapolis, Flag House Inn is near the airport and near a metro station. Looking to enjoy an event or a game while in town? See what's going on at Navy-Marine Corps Memorial Stadium. Visit our Annapolis travel guide
View more B&B in Annapolis
Map
26 Randall St, Annapolis, MD, 21401

What's nearby

  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    1 min walk - 0.1 miles
  • A white building with a dome, surrounded by lush greenery and a well-maintained garden with pathways and benches.
    William Paca House
    2 min walk - 0.1 miles
  • A town with historic buildings, a prominent church steeple, and a weather vane atop a building.
    Maryland State House
    5 min walk - 0.3 miles
  • Annapolis City Dock
    2 min walk - 0.1 miles
  • St. John's College
    6 min walk - 0.4 miles

Getting around

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

Restaurants

  • The Choptank
    3 min walk
  • Starbucks
    3 min walk
  • The Red Bean
    7 min walk
  • Iron Rooster
    2 min walk
  • McGarvey's Saloon & Oyster Bar
    2 min walk

About this property

Flag House Inn

  • Bed & breakfast near U.S. Naval Academy
  • Located close to Annapolis City Dock and Maryland State House, Flag House Inn provides free continental breakfast, a terrace, and a fireplace in the lobby. Guests can connect to free in-room WiFi.
  • You'll also enjoy perks such as:
    • Valet parking (surcharge), meeting rooms, and tour/ticket assistance
    • Concierge services and free newspapers
  • Room features
  • All guestrooms are individually furnished, and feature comforts such as premium bedding and air conditioning, as well as perks like separate sitting areas and free stocked minibars.
  • Extra amenities include:
    • Heating and ceiling fans
    • Hypo-allergenic bedding, Frette Italian sheets, and memory foam beds
    • Bathrooms with showers and free toiletries
    • 55-inch LED TVs with digital channels
    • Wardrobes/closets, separate sitting areas, and coffee/tea makers

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Frequently asked questions

Is Flag House Inn pet-friendly?

No, only service animals are welcome at the property.

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

As of Oct 24, 2026, prices found for a 1-night stay for 2 adults at Flag House Inn on Oct 26, 2026 start from $248, including 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.

How much is parking?

Self parking is available for USD 50 per night. Valet parking is available for USD 50 per night.

What time is check-in at Flag House Inn?

Check-in start time: 4:00 PM; Check-in end time: 8:00 PM. Early check-in is available for a fee of USD 95 (subject to availability). Late check-in is available from 11:00 AM– 1:00 PM for a fee of USD 95.

What time is check-out at Flag House Inn?

Check-out is at 11 AM.

Where is Flag House Inn located?

Located in Historic District, this bed & breakfast is steps from U.S. Naval Academy and Annapolis City Dock. Maryland State House and Navy-Marine Corps Memorial Stadium are also within 2 mi (3 km).

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Reviews

Flag House Inn Reviews

9.2

Wonderful

9.6

Cleanliness

10

Location

9.6

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 79 out of 99 reviews
Rating 8 - Good. 8 out of 99 reviews
Rating 6 - Okay. 5 out of 99 reviews
Rating 4 - Poor. 2 out of 99 reviews
Rating 2 - Terrible. 5 out of 99 reviews

Reviews

Verified review

10/10 Excellent

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

10/10 Excellent

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 review

8/10 Good

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

10/10 Excellent

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

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

2/10 Terrible

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 review

10/10 Excellent

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 review

6/10 Okay

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Charming and picturesque house steps from all of the best things about Annapolis.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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

2/10 Terrible

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 review

6/10 Okay

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 review

10/10 Excellent

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