Annapolis Sets $5,000 Fines for Unregistered Short-Term Rentals

Annapolis, Maryland, can now fine short-term rental operators up to $5,000 per violation for running a listing without registering with the city. The penalty applies to hosts who skip the city's licensing process or otherwise break the terms of its short-term rental rules, and it marks a harder line than the city has taken in past enforcement sweeps.

What actually triggers the fine

The top penalty applies to operators caught listing a property on Airbnb, Vrbo or Booking.com without a valid city registration on file. Annapolis requires short-term rental hosts to register before taking bookings, a rule aimed at keeping track of which properties are being rented out short-term in neighborhoods zoned primarily for long-term residential use. Hosts who have let registration lapse, or who never filed in the first place, are the ones now exposed to the $5,000 ceiling.

How the city plans to enforce it

Code enforcement in Annapolis has historically been complaint-driven, meaning violations surface when a neighbor flags a property rather than through routine city sweeps. Nothing in the new fine schedule suggests that's changing, but a $5,000 ceiling gives inspectors a much bigger stick once a complaint does land. For an operator running a single unit, a fine at the top of that range can wipe out months of net income from the property.

What hosts in Annapolis need to check now

Anyone operating a short-term rental in the city should confirm their registration is current before the next booking goes out, not after a citation arrives. That means checking renewal dates, making sure the registration number is posted where city rules require it, and keeping listings on Airbnb, Vrbo and Booking.com consistent with whatever address and unit details are on file with the city. Operators managing multiple Annapolis properties face the fine on a per-violation basis, so an unregistered portfolio carries exposure that scales with every listing left unfiled.

The move fits a pattern playing out in plenty of mid-size US cities and coastal towns, where local governments have moved from light-touch registration requirements to penalties stiff enough to actually change host behavior. Annapolis hosts who have been treating registration as optional now have a concrete reason not to.