Home/ Locations/ Annapolis
$285
Avg. Nightly Rate
55%
Avg. Occupancy Rate
$4,750
Avg. Monthly Revenue
5-7%
Est. Cash-on-Cash ROI
MEDIUM
Seasonality
HEAVY
Regulatory Burden

* Market averages. Properties marketed by Cavmir typically exceed these figures by 25–45%. Data sourced from AirDNA, STR market reports, and Cavmir internal analytics.

The Market

Why Annapolis is One of the World's Premier STR Markets

Annapolis is a small city of about forty thousand people on the Chesapeake Bay that has been the capital of Maryland since 1695 and was, for roughly nine months, the capital of the United States. The State House is the oldest state capitol still in continuous legislative use in the country, and its dome, built in the 1780s and 1790s, is the largest wooden dome in America put together without nails. The historic district around it holds an unusual concentration of surviving eighteenth-century buildings, and the street plan, with its baroque circles and radiating streets, is still the one laid out in 1696. The United States Naval Academy occupies the point where the Severn meets the bay, and its presence shapes the city's calendar in ways no other institution could. Then there is the water. Annapolis calls itself the sailing capital of the United States and the claim is defensible: the harbour is full of masts, the two boat shows in October are the largest in-water shows in the country, and a substantial part of the local economy is boats. Washington and Baltimore are both under an hour away. For an owner, this is a high-demand historic city with a genuinely unusual rulebook: the cap on short-term rentals here is measured one side of one block at a time.

Annapolis adopted Ordinance 17-25, which bars the city from issuing new short-term rental licences on a blockface once 10% of the units on that blockface are short-term rentals. A blockface is one side of one city block, which makes this one of the most finely grained caps in the country: your ability to obtain a licence depends not on a citywide number but on what the handful of properties across the street from you happen to be doing. Owner-occupied short-term rentals are exempt and do not count toward the cap, which is a substantial carve-out and the clearest route into this market for anyone willing to live here. Blockfaces already over the 10% line get a transition rather than an eviction: existing licences may be renewed until November 2027, after which the city moves to a lottery designed to bring the number back under the cap, with priority given to Annapolis and Anne Arundel County residents who already hold a licence over owners who live elsewhere. And there is one exception that tells you exactly how seriously this city takes two events: the cap does not apply during the Naval Academy's Commissioning Week or during the city's boat shows. Rental unit licences generally sit at Code Chapter 17.44. Verify the current licence fee, your blockface's position and the lottery mechanics with the City before you buy or apply.

Top Attractions & Landmarks

  • The Maryland State House and its wooden dome
  • The United States Naval Academy grounds and chapel
  • City Dock and the harbour locals call Ego Alley
  • The William Paca House and its restored garden
  • The eighteenth-century streets of the historic district
  • The Chesapeake Bay Bridge east of the city
  • Quiet Waters Park south of the historic centre

Nearby Markets: Baltimore  |  St Michaels  |  Washington DC

Airbnb marketing services in Annapolis, Maryland, USA
Why Cavmir

The Cavmir Advantage
in Annapolis

Cavmir markets Annapolis properties on the two calendars that run this city, which are the water and the Academy, and on the fact that a licensed property here is becoming a genuinely scarce thing. When a cap is measured by the blockface and a lottery is scheduled for 2027, the licence attached to your address stops being paperwork and starts being the asset. We make that legible, in the listing and on your own booking site, because a guest comparing your property with an unlicensed one elsewhere has no idea they are not comparing like with like. Then we sell the calendar properly. Commissioning Week in May, with the Blue Angels overhead and families arriving from across the country, and the sailboat and powerboat shows in October are the two moments when this city is completely full and the cap is deliberately switched off. Those dates should be priced a year ahead, not in August. Around them sits a long, pleasant sailing season, a steady government and legal trade tied to the State House, and year-round visitors to one of the best-preserved historic districts in America. We photograph the water and the walk to it, write copy that handles the parking honestly because the historic district is genuinely difficult, and build the direct booking channel. We help position and market your property. We never manage it or touch your keys.

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State of the Industry · History

The Annapolis STR Market — Past & Present

Annapolis was settled in 1649 by Puritans moving down from Virginia and became Maryland's capital in 1695, when the seat of government was moved from St Mary's City. Governor Francis Nicholson laid out a new plan for it based on baroque principles then fashionable in Europe: two circles on the high ground, one for the State House and one for the church, with streets radiating out from them. That plan is still the street plan today, which is why driving in the historic district is a puzzle and walking it is a pleasure. The eighteenth century was Annapolis's golden age. Tobacco money made it wealthy and briefly fashionable, and the Georgian houses built then survive in unusual numbers; the city is generally credited with more surviving eighteenth-century buildings than almost any other in the country. The State House, begun in 1772, is the oldest state capitol still in continuous legislative use in the United States, and its enormous wooden dome, built between 1788 and 1794 by Joseph Clark, was assembled without nails, held together with wooden pegs and iron straps. For about nine months across 1783 and 1784 the Confederation Congress met in that building and Annapolis was, in effect, the capital of the United States. Two things happened there that mattered: George Washington resigned his commission as commander-in-chief in the Old Senate Chamber in December 1783, and the Treaty of Paris ending the Revolutionary War was ratified in the same room the following month. The United States Naval Academy was established on the point in 1845 and has shaped the city ever since. Sailing became the other defining industry in the twentieth century, and Annapolis now hosts what are generally the largest in-water boat shows in the country each October. For an owner, the practical inheritance is a compact, walkable, historic city with an intense event calendar and severe constraints on parking and on building.

Pricing Strategy & Seasonality

Pricing, Seasonality & When to Capture ROI

Pricing Strategy

Annapolis has two dates that are worth more than any others and both of them are visible a year ahead. Commissioning Week at the Naval Academy in May brings families from across the country, fills every room in the city, runs at rates several times the annual average, and books extremely early. The sailboat and powerboat shows in October do the same thing for a different audience, and they are the largest in-water shows in the country. Price both a year in advance with firm minimum stays; there is no reason for caution and every reason to be early, and note that the city's blockface cap is deliberately switched off during both, which tells you how thoroughly they fill the place. Around those peaks sits a long, pleasant sailing season from spring through October, with weekends consistently stronger than weekdays. Underneath everything is a steady institutional floor: the General Assembly sits in Annapolis from January into April, which produces reliable midweek demand from legislators, lobbyists and staff during a period that would otherwise be the weakest of the year, and almost nobody markets to it. Build weekly and monthly rates aimed squarely at the session. Washington and Baltimore are both under an hour, which makes this a viable and cheaper base for visitors to either, and that is a further under-addressed audience. Remember Maryland's 6% state sales tax and the county occupancy tax sit on top of your rate.

Seasonality & ROI Windows

Two spikes and a solid base. May is Commissioning Week and the city is completely full. October brings the boat shows and the best sailing weather of the year, and it is the strongest month overall. The sailing season broadly runs April through October with strong weekends throughout, and summer brings general Chesapeake tourism plus families. Winter is the quiet stretch, but it is materially softened by the General Assembly session from January into April, which fills midweek nights with a professional audience. February is the weakest month and the right window for maintenance and reshoots.

Regulation & Licensing · 2026

What the Law Requires in Annapolis

Annapolis has one of the most finely grained short-term rental caps in the country, and understanding its geometry is the whole exercise. Under Ordinance 17-25 the city may not issue a new short-term rental licence on a blockface once 10% of the units on that blockface are already short-term rentals. A blockface is one side of one city block. That means the question of whether you can obtain a licence is answered not by a citywide register but by the handful of properties immediately around you, and it can be answered differently for two houses a hundred yards apart. Before you make an offer on anything in this city, establish the current position of that specific blockface with the City. There is a significant carve-out: owner-occupied short-term rentals are exempt and do not count toward the cap. For anyone prepared to live in the property, that is the clearest and most durable route into this market, and it is likely to remain so, because a cap designed to limit whole-house investment rentals is unlikely to be extended to resident hosts. Blockfaces already above the 10% threshold are handled by transition rather than by immediate removal. Existing licences on those blockfaces may be renewed until November 2027. After that date the city moves to a lottery intended to bring the number of licences on over-cap blockfaces back under the limit, and the lottery is weighted: priority goes to Annapolis and Anne Arundel County residents who already hold a licence, over owners who live outside the area. If you are a non-local owner on an over-cap blockface, that is a real and dated risk to your business and it should be in your financial model now rather than discovered in 2027. Finally, the cap does not apply during the Naval Academy's Commissioning Week or during the city's boat shows. Rental unit licences generally sit at Code Chapter 17.44. Verify the licence fee, your blockface position and the lottery mechanics with the City directly.

Market-Specific Tips & Challenges

Local Tips & Unique Market Challenges

Tips That Actually Move Revenue in Annapolis

Establish the blockface position before anything else, and treat it as the first question in any purchase rather than a due diligence footnote. Two comparable houses on the same street can be in completely different regulatory positions, and the seller may not know. Second, if you are or could be owner-occupied, understand what that exemption is worth. It takes you outside the cap entirely and outside the 2027 lottery, and in a city with a shrinking licensed pool that is a materially more secure position than a non-resident licence on a crowded blockface. It should also change how you market, because a resident host in a historic district has genuine local knowledge to offer. Third, price Commissioning Week and the boat shows a year out. Families booking Commissioning Week are planning around a fixed, once-in-a-lifetime date and they book as soon as they can; an owner who waits until spring has already lost the best of it. Fourth, address parking directly and early. The historic district was laid out in 1696, the streets are narrow, permit zones are real, and this is the single most common source of guest friction here. If parking is difficult, say so plainly and explain the alternative. Fifth, sell the General Assembly session, because January to April is otherwise your weakest quarter and there is a professional audience in town midweek for three months that almost no short-term rental in this city is written for.

Unique Annapolis Challenges

The blockface cap makes acquisition genuinely uncertain and requires address-level diligence that many buyers skip. The November 2027 lottery is a dated, known risk for non-resident licence holders on over-cap blockfaces, and it is weighted against them by design. Parking in the historic district is difficult and generates constant guest friction. Much of the attractive inventory is eighteenth or nineteenth century, sitting within historic district controls that restrict what can be altered and raise maintenance costs. And the demand calendar, while strong, is concentrated around two events that everyone in the city is competing for simultaneously.

The nine months Annapolis was the capital
From November 1783 to August 1784 the Confederation Congress met in the Maryland State House, which made Annapolis the working capital of the United States for about nine months. Two things happened in the Old Senate Chamber in that period that would be enough for most buildings. On 23 December 1783, George Washington appeared before Congress and resigned his commission as commander-in-chief of the Continental Army, voluntarily handing military power back to a civilian legislature at a moment when he could plainly have kept it; it is one of the more consequential things anybody has done in an American room. Then, on 14 January 1784, Congress ratified the Treaty of Paris in the same chamber, formally ending the Revolutionary War. The room has been restored to how it looked, with a figure of Washington standing roughly where he stood. The State House itself is still in use by the Maryland General Assembly, which makes it the oldest state capitol in continuous legislative service in the country.
Finance Essentials — Annapolis
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Insurance

Insure an Annapolis property on a policy written for paid guest occupancy, either a dedicated short-term rental product or a landlord policy with an explicit short-term rental endorsement, arranged in writing. Standard homeowner's cover will generally decline a guest-related claim. Ask about liability limits, loss of income and guest belongings. Two local factors dominate. The first is water. Annapolis floods, and the historic district around City Dock sees regular tidal flooding that has been increasing; flood is excluded from standard policies and is a separate purchase, so check your parcel's flood zone designation and take it seriously. Storm surge from the Chesapeake during tropical systems is a genuine exposure and wind cover may carry a separate percentage deductible. The second is the age and status of the building. Much of the desirable inventory is eighteenth or nineteenth century and sits within historic district controls, which means repairs may have to be done in specified materials and by approved methods, and that can make a claim substantially more expensive to settle; ask whether the policy carries ordinance or law coverage, which addresses exactly this. Platform host protection supplements a policy rather than replacing it.

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Property & Income Tax

Maryland applies its state sales and use tax at 6% to taxable lodging transactions, and Anne Arundel County levies a hotel or occupancy tax on top of it. Published figures for the county rate differ between sources, with both 7% and 8% reported, which is precisely the kind of discrepancy you should not resolve by guessing; confirm the current rate directly with Anne Arundel County before you publish a total or quote a figure to a guest. The county tax generally applies to short stays, with a threshold beyond which a stay is no longer treated as transient. Registration for these taxes is separate from your city short-term rental licence, and holding the licence does not register you for tax. Platforms may collect and remit some elements and not others, and the position on county occupancy tax in particular varies, so ask your platform explicitly which lines it files and file the remainder yourself; direct bookings are generally your responsibility in full, which matters in a market like this where repeat guests around Commissioning Week and the boat shows are common. Ask your accountant how the income should be treated federally and for Maryland purposes, particularly if you are operating under the owner-occupied exemption.

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Mortgages & Financing

Financing in Annapolis turns on the licence, and specifically on whether your position survives 2027. A lender underwriting short-term rental income needs to understand that the city caps licences by blockface, that owner-occupied properties are exempt from the cap, and that non-resident licences on over-cap blockfaces face a lottery from November 2027 with priority given to local residents who already hold licences. If you are buying as a non-resident on a crowded blockface, that is a dated risk to the income and a well-advised lender will treat it accordingly; be ready to demonstrate the blockface position in writing. Owner-occupied purchases are materially easier to finance for exactly this reason, and they also open the door to owner-occupier mortgage products with better terms, though you should check the loan's use covenants permit short-term letting of your home. On the property side, expect close scrutiny of anything in the historic district: appraisers and lenders look hard at older structures, and historic district controls on alterations can affect both valuation and your renovation plans. Flood zone status will also be checked, and flood insurance may be a condition of closing.

Future Outlook · 2027 & Beyond

Where Annapolis is Headed Next

November 2027 is the date to build your plan around, because it is when the transition period ends for licences on blockfaces already over the 10% cap and the lottery begins. The lottery is explicitly weighted toward Annapolis and Anne Arundel County residents who already hold a licence, which means the policy direction is clear: this city intends short-term rentals to be operated predominantly by people who live here. Anyone holding or considering a non-resident licence on an over-cap blockface should treat that as a known, dated risk rather than a distant possibility, and should be thinking now about whether the owner-occupied route is available to them. Watch the City Council for amendments to Ordinance 17-25 and for how the lottery mechanics are actually specified, since the details will matter enormously to individual owners and have not all been settled in public. On the demand side, nothing is going anywhere. The Naval Academy will hold Commissioning Week every May, the boat shows will run every October, the General Assembly will sit every winter, and the Chesapeake will keep drawing sailors. Supply is being deliberately constrained while demand stays flat or grows, which is a good position for a compliant owner with a direct booking channel and a returning guest base.

From the Desk of Sofie Sinag

Why We Love Marketing in Annapolis

Annapolis is a city of forty thousand people that was the capital of the United States for nine months, and it has never entirely got over it, nor should it. The State House is the oldest state capitol still being used by a legislature in the country, and its dome, put up in the 1780s and 1790s, is the largest wooden dome in America assembled without a single nail, held together with pegs and iron straps. In the Old Senate Chamber, George Washington resigned his commission in December 1783, which is arguably the most important thing anyone has ever done by choosing not to do something else. The street plan is the one drawn in 1696, with circles on the high ground and streets radiating out, which makes it a nightmare to drive and a delight to walk. The historic district has an astonishing number of surviving eighteenth-century buildings. And then there is the water: masts everywhere, a harbour the locals call Ego Alley because of the slow parade of boats coming in to be admired, and the largest in-water boat shows in the country every October. In May the Naval Academy holds Commissioning Week, the Blue Angels come over the Severn, and the whole city stops. We like Annapolis because it is small, old, serious and entirely surrounded by boats.

Cavmir's Annapolis Cheat Sheet

The Picks We Recommend for Your Welcome Book

Eight things to know about Annapolis before writing listing copy, in a market where your right to a licence depends on the other side of your own street.

The blockface

One side of one block

The 10% cap is measured per blockface, so two houses a hundred yards apart can be in different positions. Check yours first.

Owner-occupied

Exempt from the cap

Owner-occupied short-term rentals do not count toward the 10%. It is the clearest route in and it survives the 2027 lottery.

Commissioning Week

May, and the city is full

Naval Academy families from across the country, the Blue Angels overhead. Price it a year ahead.

The boat shows

October, sail and power

The largest in-water shows in the country. The cap is switched off for them, which tells you how full the city gets.

The General Assembly

January into April

Legislators, staff and lobbyists in town midweek for three months. Almost nobody markets to them.

Parking

The 1696 street plan

Narrow streets, permit zones and genuine difficulty. Be explicit in the listing rather than at check-in.

Flooding

Around City Dock

Tidal and nuisance flooding is regular and increasing. Check the flood zone and get proper cover.

November 2027

The lottery date

Over-cap blockfaces renew until then, after which a lottery favours local residents who already hold licences.

Local Work · Composite Case Vignettes

What Cavmir Has Done for Annapolis Properties

The three examples below are composite and illustrative. They reflect patterns common in capped historic markets, and they are not accounts of specific businesses or specific clients.

A buyer who never checked the blockface
The Brief

A purchaser was under contract on a historic district property intending to operate it as a non-owner-occupied short-term rental, working from the assumption that a citywide licence was available on application.

What We Did

We set out how the 10% blockface cap actually works, established what needed confirming with the City about that specific blockface, and explained the November 2027 transition and the lottery weighting toward local residents who already hold licences.

The Result

The buyer assessed the address against the cap before committing rather than after, and understood the 2027 exposure attaching to a non-resident licence before it became their problem.

A property that ignored the legislative session
The Brief

A well-located house priced firmly for Commissioning Week and the boat shows and then treated January through April as a write-off, discounting nightly rates without much effect.

What We Did

We built a proposition for the General Assembly session, which brings legislators, staff and lobbyists into the city midweek from January into April, equipped and photographed the property for longer professional stays, and introduced genuine weekly and monthly rates.

The Result

The weakest quarter of the year began producing consistent midweek revenue from longer bookings, and the property stopped depending entirely on two event weeks.

Commissioning Week priced in the spring
The Brief

An owner set Commissioning Week rates each March, by which time most Naval Academy families had already booked their accommodation for a date they had known about for a year.

What We Did

We moved rate-setting for both Commissioning Week and the October boat shows to a full year ahead, set minimum stays, and wrote listing copy addressed specifically to families travelling for a graduation rather than to general visitors.

The Result

Both peak periods began selling far earlier and at materially higher rates, and the property stopped competing for the leftover late bookings in its two most valuable weeks.

Ready to Grow in Annapolis?

Let's Put Your Annapolis
Property on the Map

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