Places to stay in Annapolis, Maryland

We currently have 54 accommodations in and around Annapolis. There are also other regional listings available for Motor Inns, RV parks, Hotels and other properties. You can filter these listings by the available types.

You'll discover a treasure trove of historic attractions in Annapolis, an 18th-century seaport town where Colonial-era buildings abound. Annapolis is proud to boast more existing 18th century buildings than any other city in the country! If you are visiting during the USNA’s academic year, experience the awesome sight of 4,000 midshipmen in formation at the U.S. Naval Academy as you stroll this beautiful National Historic Landmark campus. And, if you're a water and nature lover, discover a way of life indelibly linked to the Bay by exploring our 500 miles of magnificent shoreline and historic Chesapeake Bay light houses. Places to eat in the region include Annapolis Ice Cream Company, Joss Cafe & Sushi Bar, Piccola Roma, and Cafe Normandie.

If you are travelling in the area, Annapolis is located close to Fox Marsh, Regency Park Assisted Living Center, Rip Miller Field, Bodkin Point Shoal and Whitehall Bay.

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Things to see and do, places to eat in Annapolis

Photograph of Paul's Homewood Café, Annapolis
Paul's Homewood Café

Sin Fronteras Café ( Dining / Other ). Located at 2129 Forest Drive. Sin Fronteras Cafe is a Mexican-Latin American restaurant located in Annapolis and Glen Burnie, Maryland. We specialize in serving authentic Mexican and Latin American cuisine with a Miami flare! Our recipes were inspired by authentic food we enjoyed in Latin America and Mexico and our margaritas are considered the best in town! www.sinfronterascafe.com Link

O'brien's Oyster Bar & Restaurant ( Dining / Seafood ). Located at 113 Main Street. O'Brien's Steakhouse O'Brien's Steakhouse in Annapolis, Maryland is a historical and distinguished dining venue that offers the best food, the best entertainment, and the best prices. While placing emphasis on Chesapeake Cuisine, guests don't leave disappointed thanks to our unique approach to Annapolis Hospitality. obriensoysterbar.com Link

Carpaccio Tuscan Kitchen & Wine Bar ( Dining / Other ). Experience downtown Annapolis on our fountain view patio and comfortably enjoy observing the passersby. Whether you’re meeting a friend for an appetizer and glass of wine or celebrating a family or corporate event, Carpaccio Tuscan Kitchen & Wine Bar combines flavour, service, authenticity, ambiance & style to bring you all the best that Italy has to offer. www.carpacciotuscankitchen.com Link

Chart House Restaurant - Annapolis ( Dining / Steak ). Located at 300 Second Street. For more than 50 years, Chart House seafood restaurant has redefined the ideal dining experience. With 26 waterfront restaurants and showcase locations ranging from the historic to the unforgettable, Chart House specializes in dazzling views, unique cuisine and exceptional service. From fresh fish specialties, succulent steaks and slow-roasted prime rib, the renowned chefs of Chart House have tailored a menu that adds a unique touch to local flavors. www.chart-house.com Link

49 West Coffeehouse ( Dining / Coffee shop / Tea ). Located at 49 West Street. Breakfast, lunch, and dinner are served daily. Our bar offers an intriguing selection of beer, wine, spirits, and cocktails. Delectable desserts, baked goods (we make ’em!), and a full array of coffee confections–made with locally roasted, fresh coffee beans–are sure to please every palate. 49westcoffeehouse.com Link

Buddy's Crabs & Ribs ( Dining / Seafood ). Located at 100 Main Street. Buddy’s Crabs & Ribs is a family-owned and operated restaurant. We are located in the heart of the beautiful, historic district of Annapolis, and also have ample seating overlooking the breathtaking Annapolis Harbor. www.buddysonline.com Link

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