Flag House Inn Annapolis Exterior photoFlag House Inn Annapolis Facilities photoFlag House Inn Annapolis Room photo

FLAG HOUSE INN

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From$823 /night
Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

24 Randall St, Annapolis, 21401
-
Near the Annapolis Harbor
Perfect
9.0
/10
4.9
/5

5-star historic inn across from U.S. Naval Academy in Annapolis

Location

Flag House Inn sits directly across from Gate 1 of the U.S. Naval Academy. The property is a 2-minute walk from Main Street and the Annapolis City Dock. Guests can walk to the Maryland State House, boutiques, and award-winning restaurants without needing a car.

Breakfast

A gourmet breakfast is prepared each morning by a Michelin-star trained French chef. The menu includes farm-to-table omelettes, yogurt parfaits, and pastries. Breakfast is served at a single seating starting at 9:00 AM in the historic dining room.

Rooms

The inn offers 5 individually decorated rooms and a private Carriage House above the garage. Room types include the Admiral Suite, Commodore Suite, Sailing Capital Room, and the Loft. Each room has a seating area, private bathroom, and air conditioning.

Services & Amenities

On-site parking is available in a private driveway, though limited to two spots. The property provides concierge service, daily housekeeping, and a shared lounge with a TV area. Board games and puzzles are available in the common spaces.

Business & Events

Meeting and banquet facilities are available for events and weddings. The sister property, 1313 West, offers a speakeasy bar and courtyard for larger gatherings. The staff can assist with local recommendations and ticket procurement for Naval Academy events.

Highlights

Location: Across from U.S. Naval Academy, steps from Main Street

Breakfast: Gourmet farm-to-table by Michelin-star chef

Rooms: 5 unique rooms plus Carriage House

Parking: Private off-street parking available

Service: Concierge, daily housekeeping, event planning

“It's a place that feels both sophisticated and welcoming, set right where the pulse of Annapolis beats strongest. Mornings here begin with a truly exceptional breakfast, and the comfort of the beds makes winding down after a day of exploring effortless. The attentive service truly elevates the entire experience, making it feel like a personal retreat.”
Hotel logo
James DavidEditor-in-Chief at Usmaryland

Select your room type

Flag House Inn offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
  • Deluxe King Suite
    2 persons
    39 sq. feet
    2 Single beds or 1 Queen-size bed
    Air conditioning
    Bathtub
  • Double Room
    2 persons
    18 sq. feet
    1 Double bed
    Air conditioning
    Bathtub
  • King Room
    2 persons
    23 sq. feet
    1 King-size bed
    Air conditioning
    Bathtub
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
June 2026 - June 2027
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Check-in/ Check-out

Facilities

Flag House Inn offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
9.2/10Review score

General

  • No smoking on site
  • Parking
  • VIP check-in/ -out
  • Concierge desk
  • No pets allowed
  • Security
  • Coffee shop
  • Smoke detectors
  • Fire extinguishers
  • Key access

Services

  • Valet parking
  • Housekeeping
  • Tours/Ticket assistance
  • Welcome drink

Dining

  • Special diet menus

Business

  • Meeting/ Banquet facilities

Children

  • Board games

Spa & Leisure

  • Leisure/ TV room

Room features

  • Free Wi-Fi in rooms
  • Air conditioning
  • Heating
  • Sitting area
  • Garden furniture

Bathroom

  • Free toiletries

Media

  • Flat-screen TV

Room decor

  • Carpeted floor
Show more

Flag House Inn Location

24 Randall St, Annapolis, 21401
Explore Annapolis
Explore Annapolis
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
United States Naval Academy Museum
United States Naval Academy Museum
6 minutes' walk
Naval Academy history through exhibits, artifacts, and displays detailing U.S. naval heritage. Free admission for all.
Maryland State House
Maryland State House
6 minutes' walk
Historic state capitol building with stunning architecture and guided tours. Discover Maryland's legislative history.
Alumni Hall
Alumni Hall
10 minutes' walk
Home to NAC's history and traditions with picturesque grounds. A unique venue often used for ceremonies and receptions.
Annapolis Harbor
Annapolis Harbor
13 minutes' walk
Scenic waterfront featuring boat access, dining, and shops. Perfect for leisure strolls and people-watching.
Sailing on the Chesapeake Bay
10 minutes' drive
Thrilling sailing adventures available through local charters. Rentals or guided experiences offered seasonally.
Yoga by the Water
10 minutes' drive
Relaxing outdoor yoga sessions available at nearby parks. Ideal for winding down and connecting with nature.
Truxton Park
26 minutes' walk
Unwind in nature with trails, playgrounds, and picnicking areas. Great for families and leisure activities.
McGarvey's Saloon & Oyster Bar
2 minutes' walk
Casual seafood spot known for fresh oysters and a lively atmosphere. Great for group dining and casual outings.
O'Brien's Oyster Bar & Grill
3 minutes' walk
Family-friendly oyster bar serving classic seafood dishes. Offers a delightful outdoor seating area.
Dock Street Bar & Grill
2 minutes' walk
American cuisine with local beers in a welcoming environment. Perfect for quick bites and relaxed dinners.
The State Theatre of Maryland
10 minutes' drive
Live performances and shows in a historic setting. Regular events for all ages, including family-friendly programming.
The Rams Head Tavern
10 minutes' drive
Famous live music venue and pub hosting popular bands. Offers a vibrant atmosphere and extensive drink menu.
Getting around
  • City Centre
    Annapolis 8 min  ·  2000 ft
  • Airports
    Baltimore (BWI) 62 min  ·  25.4 mi
    Ronald Reagan Washington National (DCA) 90 min  ·  37.2 mi
  • Train
    Union Station Marc Washington 69 min  ·  28.5 mi
  • Bus
    Bus stop 8 min  ·  2000 ft
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Property information and rules
Check-in
from 16:00-18:00
Check-out
from 09:00-11:00
Guest Parking
Private parking is possible on site (reservation might be needed) at true.
Internet
Wireless internet is available in the hotel rooms for free.
Breakfast
At the hotel Flag House Inn guests are invited to a full breakfast served for free.
Pets
Pets are not allowed.
Number of rooms:
8

Reviews and Ratings

Feedback about Flag House Inn from previous guests about their experience.
Review score
Based on 134 verified reviews
9.4 /10
Perfect
95 %
Recommend
Cleanliness
9.6/10
Comfort
9.4/10
Facilities
9.2/10
Free WiFi
9.1/10
Location
9.6/10
Staff
9.7/10
Value for money
8.5/10
Pros
Elegant decor
Helpful staff
Really good breakfast
Immaculate rooms
Central location
Cons
Overpriced rooms
Small bathrooms
Additional parking fee
Limited accessibility
Guest reviews
based on 50 reviews
9.0/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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