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 Shady Side Elementary School, Cypress Creek Bog, Gibson Island Yacht Club, Carr Wharf and Kinder Branch.
Available accommodation types
Selected and best reviewed properties in Annapolis
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Things to see and do, places to eat in Annapolis
Chick & Ruth's Delly ( Dining / Deli ). Located at 165 Main Street. Our menu has something for everyone, from creamed chipped beef on toast to personal pizza or jumbo lump crab cakes. All pies and breads are made fresh everyday on the premises. No mixes, no preservatives, all handmade.
www.chickandruths.com 
West End Grill ( Dining / Other ). Located at 2049 West Street. West End is a sports bar restaurant that’s locally operated and independently owned. Several staff members and managers have been there for over 20 years. The culture of exceptional hospitality makes West End a favorite for locals and a warm welcoming place for visitors from all over. Enjoy the comfortable atmosphere without the corporate formalities and their sometimes robotic service routines. You’ll find that your custom requests are greeted with enthusiasm and an eagerness to fulfill your wishes.
Whether you sit in one of the quieter restaurant sections or in the bar area you will receive the same full service.
www.westendgrillannapolis.com
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
Lewnes Steakhouse ( Dining / Steak ). Located at 401 4th Street. Fine dining in Annapolis since 1921.
www.lewnessteakhouse.com
Harry Browne's ( Dining / Other ). Located at 66 State Circle. Located directly across from the Maryland State House in Historic Annapolis, Harry Browne’s Restaurant invites you to experience fine dining and award-winning cuisine in an elegant setting.
Accessed by a spiral staircase leading beneath the Grill Room, the Wine Cellar Club is a very unique private setting for members to enjoy with their friends and special guests.
www.harrybrownes.com
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
Renamed properties
- Graduate by Hilton at 126 West Street may have been previously known as Loews Annapolis Hotel or Hotel Annapolis
- Hilton Garden Inn at 174 West Street may have been previously known as The O Callaghan Annapolis Hotel
- Holiday Inn Express at 2451 Riva Road may have been previously known as Days Inn
- Crowne Plaza at 173 Jennifer Road may have been previously known as Sheraton Barcelo Annapolis
- Rodeway Inn at 74 Old Mill Bottom Road North may have been previously known as Super 8
- Sonesta ES Suites at 170 Admiral Cochrane Drive may have been previously known as Residence Inn