Annapolis, known as the “Sailing Capital of the USA” and home to the esteemed Naval Academy, offers a captivating blend of maritime history, vibrant culture, and modern amenities. Attracting over two million visitors every year, this charming city provides significant opportunities for property owners looking to tap into the short-term rental market.
However, owning a property is just the first step. To maximize your investment, understanding short term rental trends in Annapolis is essential. With a well-informed approach, your rental property can become a profitable part of your financial portfolio. Here is a detailed look at the key short-term rental trends in Annapolis.
Why Short-Term Rentals are an Attractive Investment
In recent years, the demand for short-term rentals has grown as travelers increasingly seek alternatives to traditional hotels. Short-term rentals offer property owners the chance to generate significant income from tourists and business travelers. Annapolis, with its steady stream of visitors year-round, is an ideal location for real estate investors looking to enter this booming market.
High-Demand Areas for Short-Term Rentals in Annapolis

Annapolis is an attractive destination for investment for your short term rental investment. Learn about high-demand areas for travelers.
Eastport
Eastport, situated just across Spa Creek from downtown Annapolis, combines its rich maritime roots with modern appeal. This waterfront community offers stunning views of the Chesapeake Bay making it popular among sailors and tourists seeking a blend of urban and coastal living. The area’s proximity to marinas, yacht clubs, and downtown amenities makes it an attractive option for short-term rentals, particularly for those visiting Annapolis for sailing events and festivals.
Murray Hill
Murray Hill is a historical neighborhood known for its architectural diversity, from colonial-era homes to modernized residences. Its proximity to the Naval Academy, State House, and vibrant downtown makes it highly desirable for professionals, families, and tourists. This area thrives as a rental hub, especially for those seeking a quieter stay while still enjoying easy access to major attractions.
Admiral Heights
For a more suburban feel, Admiral Heights offers larger homes and spacious yards, making it an appealing option for families. The neighborhood’s close-knit community and access to Weems Creek, parks, and community amenities make it a popular choice for both short-term and long-term rentals. Its family-friendly environment and proximity to downtown Annapolis make it ideal for visitors who want a relaxed stay near the city’s attractions.
Short Term Rental Trends: How Long to People Stay?
In Annapolis, short-term rentals often cater to weekend or week-long visitors. These guests range from tourists exploring the city’s maritime heritage to professionals attending local events. Pricing for short-term rentals typically varies based on location, property type, and seasonality.
Weekend Stays
Rates for weekend stays in Annapolis fluctuate, with prices ranging from $350 to $800 per night for entire homes, depending on the location and amenities. Waterfront properties or homes found in highly desirable areas like Eastport or Murray Hill tend to command premium prices.
Week-Long Rentals
For week-long stays, rates typically range from $1,200 to $3,500, again depending on the property’s proximity to downtown, waterfront views, and additional features like pools or large yards.
Price Fluctuations
Fall attractions and Naval Academy events, such as Commissioning Week and football games, have a significant impact on short term rental trends in Annapolis, prompting price fluctuations.
Commissioning Week
Usually the last full week of May, this is one of the busiest times of the year, with thousands of families and visitors flocking to Annapolis to celebrate the graduation of Naval Academy Midshipmen. During this week, rental prices skyrocket. Entire homes that typically rent for $350–$800 per night may surge to $800–$1,500 per night. Booking early is crucial, as many properties are reserved years in advance.
Fall Attractions
From about September to December, the fall months see an uptick in demand for short-term rentals. This is particularly so for weekends with Navy football games, and the world famous sail boat and power boat shows. Prices during game weekends and boat shows can increase by 20-40%, with rentals close to the stadium or downtown Annapolis fetching the highest rates. For instance, a property renting for $300 per night during a regular weekend might go for $450–$600 during a football weekend, especially if it’s within walking distance to the stadium, popular tailgating spots, or the temporary floating docks.
Leverage Short Term Rental Trends in Annapolis
Short term rental trends in Annapolis vary significantly throughout the year, with distinct price peaks during key Naval Academy events and the popular fall tourist season. Whether targeting weekend stays or week-long visitors, understanding these fluctuations is key to maximizing your rental income. Strategic property locations like Eastport, Murray Hill, and Admiral Heights offer ideal opportunities to capitalize on Annapolis’ steady stream of visitors.For those looking to enter the competitive short-term rental market in Annapolis or surrounding areas, Blueprints 4 Keys provides expert Airbnb management services, ensuring your property stands out and generates optimal returns during peak times and beyond.
