Fines up to $5,000 face short-term rental violators in Annapolis

The Annapolis City Council has voted to increase the maximum fine for short-term rentals from $1,000 to $5,000.

The measure -- approved at a council meeting on Monday -- aims to raise the level of compliance with current restrictions on short-term rentals across the city.  

The resolution increasing the fine for short-term rental violations to $5,000 was jointly sponsored by Annapolis Mayor Jared Littmann, Alderwoman Karma O'Neill and Alderman Brooks Schandelmeier. The higher fine went into effect immediately.

The issue of short-term rentals -- which are often booked online on sites such as Airbnb or Vrbo -- has been a much-debated topic for Annapolis in recent years. In March, the city approved a one-year moratorium on issuing new short-term rental licenses. 

A city report released in August 2025 found that nearly half of short-term rentals in Annapolis were operating without a license.

Mitchelle Stephenson, a spokesperson for the city of Annapolis, told our media partner, the Baltimore Banner, there had been 59 code violation cases for unlicensed short-term rentals since the moratorium went into effect March 9.    

The moratorium permitted existing short-term rental licenses to be renewed, but paused the issuance of new ones for one year. Owner-occupied rentals are exempt from the moratorium, along with certain high-demand events such as the U.S. Naval Academy graduation and the city's spring and fall boat shows.

Mayor Littmann told the Banner the resolution raising the fine to $5,000 came at the recommendation of city staff, who had expressed "a lot of frustration" that the existing fine did not dissuade people from operating unlicensed rentals.

A $5,000 fine is the maximum allowable by state law, Littmann said, and it is designed to be an amount that exceeds what an unlicensed rental could earn. Littmann clarified that the fine was "up to" $5,000, leaving the city with "ample room" to decide how serious a violation is.