Annapolis featuring street scenes and a city as well as a small group of people

Historic District oceanfront rentals

We found 2 oceanfront rentals — enter your dates for availability

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August 2025

September 2025

Explore Historic District ocean view rentals

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Sleeps 8 · 3 bedrooms · 1+ bathroom

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Sleeps 5 · 2 bedrooms · 1+ bathroom

Relax in the cozy king suite overlooking Historic Downtown Annapolis!

Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!

Sleeps 8 · 4 bedrooms · 3 bathrooms

Top rated ocean view rentals - Historic District

ShipShape

A home away from home. This beautiful apartment has everything an independent holidaymaker could desire. Super clean and clever design for comfort and functionality. The location is perfect for sightseeing the Annapolis historic sites and nearby colleges.

Jenny d.

Stayed May 2023

Premier Host

Fantastic house - clean, warm & perfectly located to get around Annapolis

Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!

Simon M.

Stayed Dec 2017

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