The Maryland Inn of the Historic Inns of Annapolis

We were there for boat show cruiser university. Food was great. Rooms were confetable. We did not stay at the hotel.

If you’re looking for a place with genuine historic charm in the heart of Annapolis, this hotel delivers. From the moment you arrive, it’s clear you’re stepping into a property with character—original architectural details, creaky wooden floors, and period-style furnishings that really bring out the colonial-era vibe. It’s a perfect spot if you’re a history lover or just want to soak in the atmosphere of downtown Annapolis. That said, there are a few trade-offs that come with staying in a property like this. Parking was one of the more frustrating aspects— valet will drive you in your car to one of the 3 buildings you could be assigned. You need to walk back to the main building to check out. Or drive back however there is narrow roads and very little parking. One suggestion would be to have staff operating golf carts to assist in this process. Another downside was the layout of the property: there are 3 separate buildings located in different areas of the town, so be prepared to do some walking outside to get to your room, which isn’t ideal in bad weather or if you have mobility issues. The rooms themselves had a certain old-world charm, but some felt a bit musty and could benefit from better ventilation or minor updates to make them feel fresher. Still, the overall stay was comfortable, and the location can’t be beat—just steps from shops, restaurants, and the waterfront. In short: if you’re prioritizing atmosphere, history, and a central location, this hotel is a great pick. Just be ready for a few quirks that come with staying in a historic property.

Historic charm in a prime downtown location at Duke of Gloucester and Main. Very walkable. Arrival logistics are the biggest challenge — no dedicated unloading zone, and in cold February rain it felt like a coordinated field exercise moving luggage before relocating to Hillman Garage. Room 1310 was spacious — dignitary-level square footage. Bed was adequate. Shower pressure mid. Towels softer than recent stays (4 on my ZERO to Brillo pad scale). I realize it's historic, therefore not designed for modern use ... not enough plugs for electronics. Street noise noticeable, especially enthusiastic car horn use. Charming stay overall, just be prepared for downtown logistics.

Such a cool place to stay while visiting Annapolis. Everyone from Connor at the front desk to the valets who took and brought us our car were amazing. Thanks for the hospitality!!

Was fun to stay in a historic inn. The rooms were as expected for such an old hotel, but worth staying in for the quaint, historical experience. Location was excellent. You could walk everywhere and being on Main Street there were numerous shops, restaurants and bars close by. You must visit Drummers Lot Pub under the hotel. Not a problem to check-in at Calvert House which was close. Be aware you cannot drop your luggage at The Maryland Inn until you check-in and have a key. No front desk and no way to enter hotel without your room key. Some suggestions: There was a strong deodorizer/air freshener smell in the room that was overpowering. The bottom of the tub was very slippery while showering. Being an old inn there are not many outlets. They added a plug-in adapter to address this, but we learned in the morning that the adapter did not work and none of our devices charged overnight. The bottom sheet on the bed was just a flat sheet and did not fully cover the mattress and tended to shift.

Not the biggest room, but a very charming hotel, right where you want to be in Annapolis! Steps away from shops and restaurants, with a lovely veranda to enjoy watching your surroundings. We found our room to be charming, and appointed with period furnishings. Unusual for most hotel rooms, we had three windows with nice views! Our room was a bit small for today's standards, but we were more interested in charm and atmosphere. We truly enjoyed our stay!

Wonderful location! Within walking distance of most places you would want to see, or dine.

My favorite place to stay in Annapolis. This building is part of the Historic Inns of Annapolis. Maryland Inn is at the top of Main Street on Church Circle. It's loaded with character. The rooms are well maintained even though the building is 200+ years old. I always try to reserve a room here when I am in town.