How do you define your perfect leisurely overnight stay? A historic and charming bayside town with plenty of dining, shopping and attractions within walking distance? A luxury hotel minutes away from a major airport and enormous entertainment and shopping complex? A rural escape where you can while away the time paddling a kayak on the bay or bracing yourself on a boat as you reel in dinner?

Part of what makes the Annapolis area so special is that you can find any of these appealing options here—all within close proximity to one another. Here’s a snapshot of various locales in the Annapolis area where you might want to book your next overnight visit. 

Historic downtown Annapolis 

Momentous historic landmarks dating back hundreds of year, including the Maryland State House and the United States Naval Academy. Quaint, brick-lined streets featuring adorable cottages and grand old homes. An emerging arts district on the cutting edge of cool that houses lounges with live music, trendy new restaurants, and artsy street festivals. Countless tantalizing restaurants ranging from casual pubs to white table cloth dining to the latest in tapas and other trend-setting ‘foodie’ delights. Boutique stores. Antique stores. Stores devoted to homemade fudge and fancy olive oils. Art galleries. A view of the sparkling bay. All within walking distance. This is downtown Annapolis.

Chez Amis B7B

Eastport 

Take a water taxi from City Dock or shuffle across the Spa Creek Bridge to Eastport, the laid-back maritime district of Annapolis. Eastport is where you can touch the Chesapeake: stick your toe in the water at one of the many street-end parks, rent a canoe or a kayak for a duck's-eye view of the Harbor, or immerse yourself in our watermen's heritage at the Annapolis Maritime Museum. Once a horse farm for one of Maryland's first state governors, this little peninsula is surrounded by boatyards and marinas. Severn Avenue is known as "Restaurant Row" for its wonderful selection of fine dining establishments featuring seafood and steaks, but there are laid-back sailors' pubs in the neighborhood, too, as well as galleries featuring local artists and photographers. 

Annapolis-Baltimore region 

About 10 miles from Baltimore and 25 miles from Annapolis, the Annapolis-Baltimore region has a vibrant feel all its own. Many visitors come for its incredible convenience: it’s central to BWI Thurgood Marshall Airport, a busy international airport hub surrounded by several hotels. Many visitors land at the airport, but that’s only the beginning. Annapolis-Baltimore is home to an amazing shopping-slash-entertainment complex, offering fun for the whole family. Plus, it’s the perfect launch pad to daytrips in nearby cities Annapolis, Baltimore, and Washington, D.C. Visit TheHotelsAtBWI.com for an in-depth list of hotels in the BWI/Arundel Mills Region. 

Arundel Preserve

Annapolis Countryside 

Cross over the South River Bridge from downtown Annapolis and, almost immediately, things start to feel different. The traffic dwindles, the pace slows, and you soon find yourself in the beautiful, pristine Annapolis Countryside, where much of what you'll witness appears as if time has stood still for hundreds of years. But even as you glimpse horses grazing on farmland and quaint 19th century bungalows with hammocks hanging from porches, within minutes you can arrive at a luxurious, modern, eco-friendly waterfront resort. Discover the area's history and heritage sites that tell the stories of the area's forebears. Visit small maritime villages that look like time forgot. Dine in their restaurants, featuring fresh local seafood and produce. For the true flavor of the place, come during a festival or local event. Meet the folks who live and work here-some still make a living off the land and the water. 

Herrington Habour

For a full listing of lodging accommodations in and around Annapolis, click here