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Flag House Inn

3.5 star property
Savor local breakfast specialties before relaxing by the lobby's fireplace or exploring historic downtown Annapolis moments away.

Choose dates to view prices

Flag House Inn in downtown Annapolis offers locally-sourced breakfast and free in-room WiFi. Guests can relax by the lobby fireplace or enjoy city views from the terrace. This historic B&B provides valet parking and tour assistance, earning high marks from guests.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Air conditioning
  • Parking available
  • Business services
  • Housekeeping
The current price is NT$5,864
NT$6,685 total
includes taxes & fees
Jan 4 - 2026/1/5

Room options

Available filters for rooms
Showing 5 of 5 rooms

Sailing Capital Room

Highlights

Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Free minibar items
LED TV
Hypo-allergenic bedding
Premium bedding
  • 250 sq ft
  • Sleeps 2
  • 1 Double Bed

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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Free minibar items
LED TV
Hypo-allergenic bedding
Memory foam bed
  • 150 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Chesapeake Suite

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

Chesapeake Suite

Highlights

Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Free minibar items
LED TV
Hypo-allergenic bedding
Frette Italian linens
  • 205 sq ft
  • City view
  • Sleeps 2
  • 1 King Bed

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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Free minibar items
LED TV
Hypo-allergenic bedding
Frette Italian linens
  • City view
  • Sleeps 2
  • 1 King Bed

View all photos for Fleet Suite

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

Fleet Suite

Highlights

Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Free minibar items
LED TV
Hypo-allergenic bedding
Frette Italian linens
  • 400 sq ft
  • City view
  • Sleeps 4
  • 1 King Bed and 2 Twin Beds

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  • Pet friendly
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8.8 out of 10, Excellent, 893 reviews
The price is NT$6,920
NT$7,889 total
includes taxes & fees
Jan 4 - 2026/1/5
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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
  • Maryland State House - 5 min walk - 0.4 km
  • St. John's College - 5 min walk - 0.5 km

Getting around

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

Restaurants

  • ‪The Choptank - ‬3 min walk
  • ‪Annapolis Market House - ‬2 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬3 min walk
  • ‪Starbucks - ‬3 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 breakfast (local cuisine), 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), concierge services, and free newspapers
  • Meeting rooms and tour/ticket assistance
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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134 Prince - Luxury Boutique Hotel
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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)
  • Limited onsite valet and self parking

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

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 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
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours), key retrieval

Pets

Pets not allowed (service animals are welcome, and are exempt from fees)

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

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 50.0 per stay

We have included all charges provided to us by the property.

Optional extras

  • 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

The above list may not be comprehensive. Fees and deposits may 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

We should mention

This property does not have elevators
Children 11 years old and younger are not permitted 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

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 2025/12/28, prices found for a 1-night stay for 2 adults at Flag House Inn on 2026/1/4 start from NT$5,864, 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.

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

9.4

Exceptional

9.8

Cleanliness

10

Location

9.6

Staff & service

8.6

Eco-friendliness

9.4

Property conditions & facilities
Rating 10 - Excellent. 71 out of 84 reviews
Rating 8 - Good. 5 out of 84 reviews
Rating 6 - Okay. 4 out of 84 reviews
Rating 4 - Poor. 1 out of 84 reviews
Rating 2 - Terrible. 3 out of 84 reviews

Reviews

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

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

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

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

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

10/10 Excellent

Patricia

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

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

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

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

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

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

10/10 Excellent

Dennis

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

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

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

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

10/10 Excellent

Beth

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

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

10/10 Excellent

Jason

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

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

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

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

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

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

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

10/10 Excellent

Patricia

Liked: Staff & service, room comfort
Disliked: Property conditions & facilities
We were very shocked when we arrived that the inn was under renovations. We were not told of this when we booked. The smell of paint and dust everywhere. We felt that we were inconveniencing the contractors if we had to go up or down the steps. Also all of the staircases were covered in tarp which would be dangerous for someone coming down the steps. Also your website is very deceiving. Everything we read and the pictures we saw about the inn related too the previous owners. Again it was deceiving. Website is not updated. With other B&B’s that we used in the past they all had complimentary snacks throughout the day. For example cheese and crackers or cookies and sometimes tea time. All that was complimentary was coffee and a pitcher of water. Finally, we had too ask for extra bath towels.
Stayed 2 nights in Sep 2022