This list was updated on July 29, 2024
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Still looking for a summer weekend getaway? These Annapolis Airbnbs are so close (about an hour from DC) that they’ll feel easy like a staycation, while transporting you and your crew to a quaint weekend of waterfront shopping, dining, and more.
Whether you want to relax with a Main Street stroll and a few al fresco meals, climb aboard the Woodwind—or another boat charter (kids will especially love the pirate adventure)—for a sail, check out the historic tours of the town, crack crabs, or take in the view—an Airbnb in Annapolis can serve as home base for the weekend. Here, we’ve rounded up Airbnbs with rave reviews and ample availability through the rest of the summer.
Here are seven Annapolis Airbnbs worth checking out.
“Hanover House across USNA Gate 3”
This four-bedroom, two-and-a-half bathroom renovated historic townhouse is situated downtown just across from the Naval Academy, near St. John’s College, and just a five-minute walk to City Dock and Main Street. The home has a back deck and patio area with a grill and fire pit, and sleeping accommodation for up to eight guests.
For more information about this home, click here.
“The Wardroom”
This historic three-story home has three bedrooms for up to 10 guests plus a recently updated kitchen and a private patio with outdoor dining for four. It’s an easy walk to Main Street and City Dock, and just one block from the Naval Academy.
For more information about this home, click here.
Walk to Main Street, Capital Views, Parking, and a Patio
This Duke of Gloucester Street townhome features four bedrooms with accommodations for up to eight guests. Located just behind Main Street, and a short walk to the restaurants on West Street, its top-floor bedroom offers views of the state capital.
For more information about this home, click here.
Weems Creek Cottage Annapolis
A mile and a half from downtown Annapolis’s bustling City Dock area, this studio space trades the downtown location for waterfront property. Located on Weems Creek, the two-bed cottage accommodates up to four guests, features a screened-in porch overlooking the water, and is within walking distance of West Annapolis shops and restaurants.
For more information about this home, click here.
Cozy Downtown Annapolis Studio – Walk Everywhere!
This “cozy” basement studio accommodates up to two guests just steps from a waterfront park in a quieter, more residential section of town still within blocks of all the downtown action. The rental includes toiletries including shampoo and soap as well as coffee and other snacks for all the conveniences of a hotel.
For more information about this home, click here.
Nautical Touches to This Beautiful Eastport Home
Just across the Spa Creek bridge from City Dock (easily walkable), with its own set of shops and restaurants, the charming Eastport neighborhood is the location for this two-bedroom, two-and-a-half bathroom home. The property offers off-street parking and proximity to Eastport’s “restaurant row,” Severn Avenue.
For more information about this home, click here.
A Five-Bedroom House Near the Naval Academy
Another Naval Academy-adjacent Airbnb, this home has five bedrooms and accommodates up to 10 guests with off-street parking, a patio, and a balcony—all just a few blocks away from the shops and restaurants on Main Street and Maryland Avenue.
For more information about this home, click here.
Amy leads Washingtonian Weddings and writes Style Setters for Washingtonian. Prior to joining Washingtonian in March 2016, she was the editor of Capitol File magazine in DC and before that, editor of What’s Up? Weddings in Annapolis.
