Experience the Difference: Professionally Managed by iTrip Annapolis

Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today.



Main Level Living

Enter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV.



The adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance.



Parking: No on-site parking. One dedicated space is provided in a nearby garage (10-minute walk). The garage charges a one-time $5 per vehicle service fee. Please contact us for parking details.



SLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 8:

Top Floor King Suite:

King Bed

Ensuite Full Bath with double vanity, shower/bathtub combo and walk-in closet



2nd Floor King Suite:

King Bed

Ensuite Full Bath with stand-up shower



2nd Floor Queen Guestroom

Queen Bed

Full Bath in the Hall with shower/bathtub combo



Main Level

Full Sleeper Sofa

Powder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor



Amenities & Highlights

Private fenced yard with Adirondack seating and propane grill

Fully equipped kitchen

Dining table with seating for 6

WiFi & big screen TVs in every bedroom and the Family Room

Luxury linens & complimentary starter toiletries

Washer & dryer inside the home

Contactless check-in via coded front door entry

Non-smoking property



Property Distance to:

- U.S. Naval Academy – 2 blocks

- Washington, DC – 30 miles

- Baltimore - 25 miles



*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.

* All beds are ready made for you with freshly laundered sheets & towels.



House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood.

Check-in time: 4:00 pm

Check-out time: 11:00 am



Blending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration.