Annapolis feels made for harbor light, brick streets, and slow footsteps.
Best Stays by Sonder Annapolis
Find places to stay in Annapolis. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
Maritime history, measured pace, brick streets.
Annapolis moves at a measured harbor-city pace, where brick streets, the Maryland State House, and views along City Dock give the city a maritime character that lingers.
What Makes Annapolis Annapolis
- Brick lanes to the harbor
- State House on the hill
- Naval Academy marching cadence
- Crab houses and dockside tables
- Sails moving through Ego Alley
- Old streets with water nearby
Where to Stay in Annapolis
Annapolis Popular Stays
Choose your perfect stays
-
Parking -
Pool -
Balcony/Terrace -
Kitchen
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Breakfast -
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Parking
-
Pool
-
Ocean View -
Balcony/Terrace
-
Breakfast
-
Parking
-
Pool
-
Kitchen
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
Good for the Weekend
Easy in-and-out for quick Annapolis gateway.
Work-friendly stays
Desks, fast Wi-Fi, and a kitchen for work trips that run long, with dinner a short walk away.
Historic streets and harbor-side rhythms.
Annapolis feels walkable and harbor-close, with a measured pace that favors wandering, dining, and easy city stays.
Known for
U.S. Naval Academy, the Maryland State House, and a compact maritime heritage scene give Annapolis its historic edge, with brick streets, harbor views, and a deep naval identity.
Best for
First visits, history-focused weekends, and work trips that stretch into a slower city break, especially if you want museums, civic landmarks, and easy evenings out.
Walkability
Downtown and the Historic District are easiest on foot, with narrow streets, waterfront blocks, and short links between landmarks, shops, and restaurants.
Closest airport
Baltimore/Washington International Thurgood Marshall Airport (BWI) is the primary commercial airport, located northwest of Annapolis.
Ideal trip length
Two to three days gives you time for the core sights, a measured waterfront stroll, and a relaxed meal or two without rushing between them.
Vibe
Historic, maritime, polished, unhurried
What Annapolis leaves in your memory.
From dockside walks to brick-lined streets, the things to do in Annapolis feel shaped by the harbor and State Circle.
Pick up pastries at the farmers market
Early shoppers drift through the Anne Arundel County Farmers' Market for coffee, produce, and baked goods, then linger over a quick catch-up before heading back downtown.
Stroll Main Street before lunch
Locals move along Main Street for errands, a bookstore stop, or a casual bite, with brick sidewalks and storefronts shaping an easy midday rhythm.
Grab takeout near City Dock
Order coffee or lunch from nearby counters and carry it toward City Dock, where people pause at the water's edge for a simple break in the day.
Browse shops along West Street
West Street mixes everyday shopping with low-key dining, so you can wander between small businesses, pick up essentials, and settle in for an unhurried meal.
Every few blocks, a different side of Annapolis
From colonial streets to harbor edges, each area moves at its own pace and shapes a different stay.
A year of harbor-side rhythms.
Many travelers aim for September, when the Annapolis Boat Shows bring the harbor and downtown into focus.
Spring
Downtown wakes into a lighter pace, with sailors, students, and locals moving between brick streets, harbor views, and cafe tables as daylight settles softly over the center.
Summer
Evenings stretch along the waterfront and through the historic core, where diners spill onto sidewalks and the city moves at a slower, lingering rhythm after work.
Fall
The streets feel crisp and focused, with a steadier tempo around the academy, the shops, and the waterfront as weekends fill with game-day energy and season-openers.
Winter
The historic core turns quieter and more intimate, with decorated storefronts, warm dining rooms, and an easy, unhurried rhythm that rewards short walks and lingering stops.
Annual events worth planning around
Annapolis Film Festival
A spring film festival with screenings, panels, and conversations across downtown theaters and venues.
Annapolis Fourth of July Parade
A long-running summer parade through the downtown streets, typically held in early July.
United States Sailboat Show
An October sailing showcase along the waterfront, drawing boat builders, gear, and maritime crowds.
Midnight Madness
A December downtown shopping tradition with extended evening hours, holiday lights, and seasonal festivities.
Locals’ go-tos, all week.
From State Circle coffee stops to quiet Dock Street routines, these are the Annapolis places locals keep coming back to.
Walk Main Street before the shops open
Morning light on brick sidewalks, courthouse views, and coffee stops near the State House. It is a steady Annapolis ritual for people heading downtown.
Grab a crab cake at Chick & Ruth's Delly
A long-running downtown counter where locals linger over breakfast plates, sandwiches, and Maryland crab cakes. The room feels like a daily stop, not an outing.
Catch a show on West Street
Ram's Head On Stage draws neighbors for live music and an easy night out. Around it, West Street gives you restaurants, bars, and an after-dinner walk.
A few things worth knowing.
From the most walkable neighborhoods to how travelers explore the city, these notes help you plan a trip to Annapolis.
Most walkable areas
Historic Downtown and the City Dock area make the easiest foot loop, with the Maryland State House nearby.
Getting around
Annapolis works well on foot in the center. Use a car for farther neighborhoods, or follow local buses where they fit your route.
Ideal trip length
Two to three nights gives time for the historic core, harbor views, and a slower pace on the side streets.
Good for work trips
Stay near Downtown for quick access to offices, restaurants, and walkable evenings, with apartment-style space where available.
Annapolis travel questions, answered.
Quick answers to the questions travelers ask most.
Annapolis is very walkable in the historic core, where many shops, restaurants, and waterfront sights are easiest to reach on foot. If you plan to explore beyond the center, a car can make the trip simpler, especially for wider area errands or day outings. For a stay focused on downtown, you can often rely on walking and short rides.
For a first visit, stay close to the historic center if you want the simplest access to dining, waterfront strolls, and the city’s main sights. That area keeps you near the rhythm of the city without much planning. If you prefer a quieter base or easier driving access, look just outside the core and compare the listing details.
Two to three days is enough for a focused visit if you want time for the main streets, waterfront areas, and a relaxed meal schedule. A longer stay works well if you like moving slowly, browsing neighborhood spots, or mixing in remote work. If your itinerary is only one night, choose a central stay so you spend less time in transit.
Annapolis can feel busiest on weekends, during special events, and in warmer months when more people are out walking the center. If you want a calmer stay, weekdays are often easier for dining reservations, parking, and getting around. Exact crowd levels vary by season and event calendar, so it helps to check your travel dates before booking.
Yes, Annapolis can work well for business travel or a remote-work stay if you want a central base with easy access to cafes, meetings, and the walkable core. Many stays offer work-friendly setups, but amenities vary by building, so check the listing for desk space, Wi-Fi details, and other essentials before you book.
Go with curiosity. Come back with stories.
The best trips rarely go exactly as planned. Sonder keeps you closer to the neighborhoods, kitchens, and small moments that make a city worth remembering.