Annapolis, Maryland Short-Term Rental Market
Annapolis caps new STR licenses by blockface; September 2026 ADR $199, occupancy 56.2%, revenue $3,069 monthly.
Quick Answer: Annapolis, Maryland is an active short-term rental market. average occupancy in the Baltimore market area is 56%. average monthly revenue in the Baltimore market area is $3,069. average daily rate in the Baltimore market area is $199. the top operator in the Baltimore market area is Evolve with 89 listings. market score is 61/100 (grade C).
Market data reflects the Baltimore regional market, which includes Annapolis. Regulations, taxes, and permit details below are specific to Annapolis.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Annapolis, Maryland is a regulated short-term rental market, and the latest data month is September 2026. In September 2026 the average daily rate across all listings was $199, occupancy was 56.2%, and the average listing earned $3,069 in monthly revenue. Compared with a year earlier, occupancy is down 1.9%, ADR is up 3.7%, and revenue is up 7.8%, so rate growth more than offset softer bookings. The market is large for a city of 40,689 residents. The Annapolis area STR market tracks 5,122 listings, made up of 3,690 entire places, 1,429 private rooms, and 3 shared rooms. By bedroom count, one-bedroom units lead with 2,483 listings, followed by 1,071 two-bedroom, 837 three-bedroom, 464 four-bedroom, and 256 five-bedroom listings. By channel, 3,269 listings appear on Airbnb only, 298 on Vrbo only, and 1,555 on both platforms. Demand is anchored by tourism. Annapolis and Anne Arundel County drew 7.2 million visitors in 2024, generating $4.3 billion in economic impact, and visitors spent $480 million on lodging. Main draws include the United States Naval Academy, the Maryland State House, City Dock, and the Annapolis Sailboat Show and Powerboat Show each October. Commissioning Week each May adds further demand, and Washington D.C. and Baltimore are each about 30 miles away, which supports day trips and weekend stays. On a calendar basis, 2026 through September shows occupancy of 58.1%, ADR of $170, and monthly revenue of $2,737, against 57.3%, $164, and $2,636 for full-year 2025. Investors should read the regulatory section carefully, because a blockface cap now limits new licenses in the most sought-after parts of the city.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 48% |
| Feb | 57% |
| Mar | 59% |
| Apr | 60% |
| May | 64% |
| Jun | 66% |
| Jul | 65% |
| Aug | 63% |
| Sep | 59% |
| Oct | 58% |
| Nov | 54% |
| Dec | 53% |
Month-by-month nightly rates and revenue figures for Annapolis are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Baltimore market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Baltimore market as a whole, which includes Annapolis, so these counts are not Annapolis-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 89 | 2,349 | ★ 4.32 |
| 2 | ITrip Vacations | 79 | 2,393 | ★ 4.90 |
| 3 | PMI Annapolis Property Management Company | 28 | 681 | ★ 4.91 |
| 4 | Vacasa | 26 | 567 | ★ 4.67 |
| 5 | Sure Rental Company | 24 | 48 | ★ 4.94 |
What Kind of STR Should I Buy in Annapolis?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Annapolis are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 63.8% |
| vrbo | 5.8% |
| both | 30.4% |
Home Value Trends (Annapolis)
Typical home values, median sale prices, and the 10-year price trend for Annapolis are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Annapolis — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Annapolis permits short-term rentals but has one of the more restrictive local frameworks in Maryland. A city Short-Term Rental License is required and costs $500 per year, renewed annually. A short-term rental is defined as a stay under 120 consecutive days, which also works as the maximum stay per booking. The key recent change is Ordinance O-17-25, passed in October 2025. No new licenses may be issued on any blockface where 10% or more of residential units are already licensed STRs, and blockfaces with fewer than 10 residential units are capped at 1 license. Currently 42 blockfaces exceed the cap: 30 in Ward 1, 5 in Ward 2, and 7 in Ward 8. Existing over-cap licenses can renew through November 2027, after which a lottery takes effect that prioritizes local Annapolis and Anne Arundel County residents. Owner-occupied STRs are exempt from the cap count. STRs are prohibited in Accessory Dwelling Units. Non-resident owners must designate a property manager within city limits. A safety inspection is required before a license is issued. Maximum occupancy is 2 guests per bedroom plus 2 additional, up to 10 total, and quiet hours run from 10 PM to 7 AM. Occupancy tax is 8% of gross rent, up from 7% in July 2023, in addition to Maryland’s 6% state sales tax. Neither owner occupancy nor primary residence is required. Penalties start at a $1,000 fine for a first offense and escalate to suspension and permanent revocation. Enforcement is rated moderate. Confirm current rules with the City of Annapolis before buying.
Market Comparison
Within Annapolis, September 2026 occupancy was 56.2% and the all-listings ADR was $199. Entire homes at $256 and professionally managed listings at $353 sit well above the blended rate, and luxury listings at $443 are more than double it. That suggests Annapolis rewards well-positioned whole-home inventory, while the large share of private rooms and one-bedroom units holds the blended rate down. Professional operators have a real presence. In the Annapolis area STR market, the largest managers are Evolve with 89 listings, ITrip Vacations with 79, PMI Annapolis Property Management Company with 28, Vacasa with 26, and Sure Rental Company with 24. Ratings for these operators range from 4.3 for Evolve to 4.9 or higher for ITrip Vacations, PMI Annapolis, and Sure Rental Company, so guest expectations are high. Investors should compare their own plans with these operators on both rate and review quality. Overall, Annapolis offers a gross yield of 4.2% and a regulatory structure that limits new supply on many blocks.
Frequently Asked Questions About Annapolis, Maryland
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