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Annapolis stays by Sonder

Annapolis feels made for harbor light, brick streets, and slow footsteps.

Sonder Annapolis Places to Stay

Annapolis moves at a measured pace, where historic streets invite lingering turns and return visits.

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A scene in Annapolis
About Annapolis

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
Annapolis stays

Pick the part of the city to wake up in.

Stays grouped by the way people travel, so you can start from the trip you want rather than a list of rooms in Annapolis.

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Aparthotels in Annapolis

Over 4+ Apartment-Style Stays with Hotel Comfort in Annapolis
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Business Hotels & Aparthotels in Annapolis

Over 9+ Work-Friendly Stays for Business Trips in Annapolis
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Annapolis at a Glance

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

The Annapolis Experience

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.

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.
Locals move along Main Street for errands, a bookstore stop, or a casual bite, with brick sidewalks and storefronts shaping an easy midday rhythm.
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.
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.
Neighborhoods of Annapolis

Every few blocks, a different Annapolis.

From historic streets to leafy waterfront, each neighborhood offers its own way
to spend a day in the city.

Historic District

Historic District
Eastport

Eastport
Murray Hill

Murray Hill
West Annapolis

West Annapolis
Arundel on the Bay

Arundel on the Bay
Homewood

Homewood
Hillsmere

Hillsmere
Epping Forest

Epping Forest
Oyster Harbor

Oyster Harbor
Anchorage

Anchorage
Atlantis

Atlantis
Winchester-on-the-Severn

Winchester-on-the-Severn
Cape St. John

Cape St. John
Hunt Meadows

Hunt Meadows
Kingsport

Kingsport
Downs on the Severn

Downs on the Severn
When to Visit Annapolis

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.

Highlights Annapolis Spring Sailboat Show, United States Naval Academy Commissioning Week, Maryland Day

Tip Spring suits travelers who want the city’s maritime rituals and public life in easy view.

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.

Highlights Wednesday night sailboat races on Spa Creek, First Sunday Arts Festival, summer concerts at the Annapolis City Dock area

Tip Summer works well if you want long, social evenings and time to wander between dinner, music, and the harbor.

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.

Highlights United States Naval Academy home football games, Annapolis Boat Shows, First Sunday Arts Festival

Tip Fall suits travelers who like a sharper city pace and a calendar shaped by tradition.

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.

Highlights Midnight Madness, Annapolis Chocolate Binge Festival, Eastport Yacht Club Lights Parade

Tip Winter is a good fit if you prefer smaller crowds, holiday atmosphere, and time indoors between downtown stops.

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.

Highlights Annapolis Spring Sailboat Show, United States Naval Academy Commissioning Week, Maryland Day

Tip Spring suits travelers who want the city’s maritime rituals and public life in easy view.

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.

Highlights Wednesday night sailboat races on Spa Creek, First Sunday Arts Festival, summer concerts at the Annapolis City Dock area

Tip Summer works well if you want long, social evenings and time to wander between dinner, music, and the harbor.

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.

Highlights United States Naval Academy home football games, Annapolis Boat Shows, First Sunday Arts Festival

Tip Fall suits travelers who like a sharper city pace and a calendar shaped by tradition.

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.

Highlights Midnight Madness, Annapolis Chocolate Binge Festival, Eastport Yacht Club Lights Parade

Tip Winter is a good fit if you prefer smaller crowds, holiday atmosphere, and time indoors between downtown stops.

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.

Notes that 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.

Good to know

Annapolis travel questions, answered.

Quick answers to the questions travelers ask most.

01 / 07
What are the top Boutique Hotels and Aparthotels in Annapolis?

Discover top family-friendly travel options in or near Annapolis. If you're planning a trip or vacation to Annapolis, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in Annapolis:

02 / 07
How many Boutique Hotels, Aparthotels, and Urban Apartments are available in Annapolis?

Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 26 active properties listed by Sonder in 2026 in the Annapolis area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting Annapolis.

03 / 07
Is Annapolis walkable, or will I need a car?
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.

04 / 07
What part of Annapolis should I stay in for a first visit?
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.

05 / 07
How many days should I plan for a trip to Annapolis?
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.

06 / 07
When is Annapolis busiest for visitors?
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.

07 / 07
Is Annapolis a good place for a work trip or remote work stay?
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.

Discover top family-friendly travel options in or near Annapolis. If you're planning a trip or vacation to Annapolis, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in Annapolis:

Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 26 active properties listed by Sonder in 2026 in the Annapolis area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting Annapolis.

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.

More places worth discovering.

Explore Annapolis neighborhoods

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