Annapolis Raises STR Fines to $5,000: What Hosts Must Know Now

If you are running a short-term rental in Annapolis without a license, the city just made that gamble a lot more expensive. The Annapolis City Council has raised the maximum penalty for illegal short-term rentals to $5,000, a figure that is five times what the previous maximum used to be. This is not a warning shot. It is a direct escalation aimed at operators who have been ignoring the rules.

What the Council Just Did

On September 29, 2026, the Annapolis City Council approved a resolution hiking the maximum fine for short-term rental violations. The new ceiling of $5,000 replaces a penalty that was one-fifth as large. The vote signals that city officials are done treating non-compliance as a minor administrative nuisance. For hosts who have been operating without a license or outside the rules, the cost of getting caught just jumped to a level that can wipe out months of rental income in a single citation.

The Numbers That Matter

The fine increase is the headline, but it sits inside a broader compliance framework that already has real costs. Annapolis requires hosts to hold a Short-Term Rental license, which runs $400 per year. The city also requires a local contact, meaning you cannot simply list a property and disappear. On the tax side, hosts owe an 8% local tax rate on rental revenue, submitted manually on a monthly basis through the city's portal. The county tax rate is also 8%. None of that is optional, and the new fine structure makes ignoring any piece of it far more costly than before.

Why This Matters More Than a Typical Fine Increase

A fivefold jump in the maximum penalty is not a routine adjustment for inflation. It is a policy statement. Cities that want to seriously reduce illegal STR activity use fines large enough to exceed the profit from non-compliance. At $5,000 per violation, Annapolis is now in that territory. Hosts who have been calculating that the risk of a small fine was worth skipping the $400 annual license need to redo that math immediately. The calculus has changed completely.

What Compliant Hosts Should Do Right Now

If you are already licensed, keep your paperwork current and make sure your local contact information is up to date. If you are not licensed, the path forward is straightforward even if it requires some effort.

• Apply for your Short-Term Rental license through the city's portal at css.annapolis.gov. The fee is $400 per year.
• Designate a local contact as required by city rules.
• Register for monthly tax remittance and submit your 8% local tax on rental revenue every month through css.annapolis.gov.
• Review the city's official guidance at the Applying for a Short Term Rental page.

The window for treating Annapolis STR compliance as optional has closed. With a $5,000 maximum fine now on the books, the cost of a single enforcement action dwarfs the annual cost of getting licensed and staying current on taxes. Get compliant before the city comes looking.

For the complete Annapolis compliance guide including tax calculator, checklist, and daily monitoring, see Annapolis, MD STR Regulations.