217 rooms in the Art District with a collegiate boutique interior that quietly references the Naval Academy, six blocks from City Dock and one of the few mid-price stays in town that feels properly designed.
"The Graduate makes the Annapolis four-star bracket interesting again. The references to the Naval Academy are tongue-in-cheek rather than reverential, the rooms are sharper than the price band suggests, and the lobby bar is the most consistently good cocktail room in the Art District."
The Graduate by Hilton Annapolis sits at 126 West Street, on the western edge of the Annapolis Art District, six blocks from City Dock and roughly a ten minute walk from the United States Naval Academy main gate. The property opened under the Graduate flag in 2017 inside what was previously the Loews Annapolis, and absorbed the Hilton co-brand in 2024 after Hilton acquired the Graduate portfolio. The exterior brick massing is essentially unchanged from the Loews era; the interior is where the Graduate identity does its work.
The lobby reads as a freshly minted college library. Tartan wool, hand-illustrated wallpaper, a long bar in dark stained oak, a wall of bookplates, and the consistent collegiate motif of small framed nods to the Brigade of Midshipmen. The reference is light, not parodic, and the room has become a destination on its own for the post-Hill crowd. There are 217 rooms across seven floors, in categories from a 280 square foot Standard King to the corner 720 square foot Premier Suite with the West Street view. The room design palette is restrained, navy upholstery, brass fixtures, a single signed print, with a thoughtful millwork desk that actually works for a laptop and a working group of two.
The food and beverage program is concentrated in two outlets. Poindexter on the lobby level runs a daylong American menu with a strong breakfast and a respectable raw bar at dinner; Camp Wow on the rooftop, the property's signature, opens seasonally from April to October and is the most reliable rooftop reservation in Annapolis on a summer Saturday. There is no full-service spa; an in-room massage program and a 24-hour fitness floor cover the wellness brief. The conference floor holds 14,000 square feet of meeting space across nine rooms, which is what keeps the property at the centre of the Annapolis corporate calendar.
Service runs warm and properly trained. The front office is one of the better recruited in town and the bell team genuinely knows the Naval Academy parade schedule and the Eastport restaurant rotation, which matters at this price point because the Graduate is where Plebe Parents Weekend and Commissioning Week largely book. Valet is the realistic option; the surface lot is small and the city's metered streets fill by mid-morning. WiFi is free, fast, and stable across the building, which is unusual at this room count.
For an Annapolis anniversary in the four-star bracket, the Graduate hits the brief without overreaching. Book a Premier King with West Street view, plan dinner at Camp Wow for the rooftop sunset over the Naval Academy chapel dome, and use the second day for the City Dock and Eastport walk. The room product is comfortably above what the rate implies, which is exactly what a milestone weekend wants.
For Annapolis business, the Graduate is the default booking for any group between 20 and 200 attendees. The 14,000 square feet of meeting space is divisible, the catering kitchen is competent, and the bedrooms double as proper work spaces. The lobby bar is also where the relevant Annapolis crowd actually drinks, which makes informal client dinners cheaper to engineer than at the harbor properties.
126 West Street
Annapolis, MD 21401
United States
Ten minutes on foot to City Dock and the Naval Academy main gate
217 rooms across seven floors
Standard Kings from $160/night
Premier Kings from $230/night
Premier Suite from $420/night
Check-in: 4:00 PM
Check-out: 11:00 AM
Pet friendly (one-time fee). Valet parking available.
Poindexter (all-day American restaurant)
Camp Wow (seasonal rooftop bar)
24-hour fitness centre
14,000 sq ft of meeting space
Free high-speed WiFi throughout
From $160/night. Premier categories and rooftop tables book three to four months ahead for Commissioning Week (late May) and Plebe Parents Weekend (August); two weeks for most autumn and winter dates.
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