Annapolis' downtown mixes colonial brick streets, the Chesapeake Bay, and the U.S. Naval Academy-so hotels here sit in the middle of it all. Options range from the Graduate by Hilton, with its modern restaurant and free bikes near the State House, to the 1313 West Luxury Boutique Hotel, a superb-rated property 4.1 km from Annapolis Harbor offering free parking and a garden terrace. Expect to pay a mid-range to premium price for the location, but you can also find budget-friendly picks like the Fairfield by Marriott Inn & Suites, 1.8 km from the State House, which includes breakfast and an electric vehicle charging station.
For a true historic feel, stay at the Flag House Inn or Historic Inns of Annapolis-both set in 18th-century buildings within a short walk of Main Street and the harbor. The Westin Annapolis gives you a modern base with an indoor pool, while the Capital Hotel Annapolis suits travelers wanting easy access to the Naval Academy and restaurants. Most properties offer free WiFi, some include parking (a rare perk downtown), and all are within 2 km of the water. To lock in the best rate, book directly on Booking.com and filter for free cancellation. Check room availability now and compare live prices for your dates.