Flag House Inn | Bed & Breakfast in Annapolis

Q: How much does it cost per night to stay in Flag House Inn?

Best-rates for the Flag House Inn starts from $255 per night with includes Balcony/Terrace, Business Services, Bar, Bedding/Linens, Breakfast, Laundry, Wellness Facilities, Toiletries, Guest Services, Air Conditioner, Parking, Designated Smoking Area, Fireplace/Heating, Internet, Kitchen, TV With private courts and nearby facilities. PickleTrip™ offers a wide range of properties for pickleball players and travelers of all types. Our goal is to connect you with the perfect vacation rental, resort, or hotel that has a private pickleball court or nearby facilities, ensuring a fun and active stay.

| 9.2 (89 Reviews) | 1 Bedroom 1 Bathroom

Historic District Bed & Breakfast | Flag House Inn

1 Bedroom Bed & Breakfast in Historic District, Annapolis

Valet parking, a refrigerator in a common area, and concierge services are available at this bed & breakfast. Free continental breakfast and free WiFi in public areas are also provided. Additionally, self parking, free newspapers, and tour/ticket assistance are onsite.
flag house inn offers 5 accommodations with free minibar items and espresso makers These individually decorated and furnished accommodations have separate sitting areas. Memory foam beds feature Frette Italian sheets and premium bedding. 55-inch LED televisions come with digital channels.

bathrooms include showers, complimentary toiletries, and hair dryers Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include complimentary newspapers and complimentary bottled water. Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided daily.

26 Randall St, Annapolis, 21401, USA

Amenities

Air Conditioner

Parking

Designated Smoking Area

Balcony/Terrace

Business Services

Bedding/Linens

Wellness Facilities

Fireplace/Heating

Bar

Toiletries

Guest Services

Breakfast

Internet

Kitchen

Laundry

Facility Overview

Bathrooms

Toilet paper

Towels

Shampoo

Hair dryer

Private bathroom

Shower

Toothbrush and toothpaste (on request)

Free toiletries

Soap

Bedroom

Frette Italian sheets

Bed sheets

Ceiling fan

Memory foam mattress

Air conditioning (climate-controlled)

Premium bedding

Heating (climate-controlled)

Hypo-allergenic bedding

Separate sitting area

Restaurant dining guide

Electrical adapters/chargers

Iron/ironing board (on request)

Individually furnished

Free newspapers

Guidebooks/recommendations

Window screens

Individually decorated

Breakfast

Free continental breakfast available daily 8:00 AM–10:00 AM

Free minibar

Free bottled water

Coffee/tea maker

Espresso maker

Parking

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

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

Accessibility

If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.

Thin carpet in room

Upper floors accessible by stairs only

Handrails in hallways

This property does not have elevators

Handrails in stairways

Well-lit path to entrance

Entertainment

55-inch LED TV

Digital channels

General

Meeting rooms

Free newspapers in lobby

English

Designated smoking areas

Shared refrigerator

Fireplace in lobby

Guest Services

Tour/ticket assistance

Concierge services

Daily housekeeping

Front desk (limited hours)

Internet

Available in some public areas: Free WiFi

Available in all rooms: Free WiFi

Outdoors

Terrace

Policies

Check-in

Check-in start time: 4:00 pm; check-in end time: 8:00 pm contactless check-in available early check-in fee: usd 95 early check-in subject to availability 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

Child Policy

Children 11 and younger are not allowed at this property. all guests older than 11 are welcome. rollaway/extra beds are not available.

Payment Policy

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.

Pet Policy

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

Cashless transactions are available 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 masks are required at the property for guests without covid-19 vaccination safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit 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

Reviews

Elizabeth

Nov 15, 2025 02:42:57 AM

Review Score: 10

Summary: 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.

See All Reviews

Room Arrangement

Room Info	Facilities
Fleet Suite Room Size: 400 square feet m² 3 King Bed and Twin Beds	General No cribs (infant beds), Number of bedrooms - 1, Ping - 11, Square meters - 37, Bed count maximum 3, Square feet - 400, City view, Bed count minimum 3
Sailing Capital Room Room Size: 250 square feet m² 1 Double Bed	General Hair dryer, Thin carpet in room, Frette Italian sheets, Number of bedrooms - 1, Ping - 7, Square feet - 250, Laptop-friendly workspace, Towels provided, Premium bedding, Square meters - 23, Location - ground floor, Desk, No cribs (infant beds), Hypo-allergenic bedding available, Courtyard view, Bed count minimum 1, Bed count maximum 1
Chesapeake Suite Room Size: 205 square feet m² 1 King Bed	General Square feet - 205, Ping - 6, Square meters - 19, No cribs (infant beds), Number of bedrooms - 1, Location - top floor, Bed count minimum 1, Bed count maximum 1, City view
Commodore Suite Room Size: m² 1 King Bed	General No cribs (infant beds), Number of bedrooms - 1, Location - top floor, Bed count minimum 1, Bed count maximum 1, City view
Loft Suite Room Size: 150 square feet m² 1 Queen Bed	General Memory foam mattress, Hair dryer, Ping - 4, Thin carpet in room, Frette Italian sheets, Number of bedrooms - 1, Square meters - 14, Premium bedding, Square feet - 150, No cribs (infant beds), Hypo-allergenic bedding available, Courtyard view, Access via exterior corridors, Bed count minimum 1, Bed count maximum 1

FAQ's

Is this Flag House Inn pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Flag House Inn have a swimming pool?

No, this Flag House Inn does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Flag House Inn?

Best-rates for the Flag House Inn starts from $255 per night with includes Balcony/Terrace, Business Services, Bar, Bedding/Linens, Breakfast, Laundry, Wellness Facilities, Toiletries, Guest Services, Air Conditioner, Parking, Designated Smoking Area, Fireplace/Heating, Internet, Kitchen, TV With private courts and nearby facilities. PickleTrip™ offers a wide range of properties for pickleball players and travelers of all types. Our goal is to connect you with the perfect vacation rental, resort, or hotel that has a private pickleball court or nearby facilities, ensuring a fun and active stay.

Is Flag House Inn a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is not considered to be a family-friendly property. As reported by the owner or manager, the bed & breakfast has not specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Flag House Inn wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Flag House Inn has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Flag House Inn?

Based on the information reported by the owner or manager, the Flag House Inn indicates 1 day stay policy at this bed & breakfast. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Flag House Inn?

Based on the information reported by the owner or manager, details for the cancellation policy for the Flag House Inn are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check Bed & Breakfast Availability

Nightly rates from:

US $255