Stevensville, MD STR Market Report 2026: Kent Island's Own Year

Jacob Mishalanie
5 days ago
12 min read

Christ Church historic landmark in Stevensville Maryland photograph

Drive across the Bay Bridge from Annapolis and Stevensville announces itself before you've found a parking spot: marina masts, a Rite Aid next to a bait shop, and a two-lane road that still remembers being a fishing village before it became Kent Island's commercial spine. Hosts who buy in on the strength of a regional Eastern Shore pitch — the one built around Chestertown's brick storefronts and colonial walking tours — end up marketing the wrong town. Stevensville isn't a smaller Chestertown. It's a bridge-adjacent, boat-adjacent, unincorporated stretch of Queen Anne's County that draws a different guest on a different calendar.

That distinction matters more than it sounds like it should, because the two towns keep getting filed together in regional roundups, and the regulatory and revenue pictures genuinely don't match. This report treats Stevensville as its own market: what AirROI's data actually shows, what the county's short-term rental ordinance actually requires, and where the neighboring towns' numbers stop being relevant to a Stevensville listing.

For a host or a buyer trying to size this market honestly, the temptation is to reach for whichever regional figure sounds most favorable and build a pitch around it. That's how a Chestertown revenue year or an Annapolis occupancy figure ends up quietly pasted into a Stevensville listing description or a purchase pro forma. This report is built to make that mistake harder — every figure here is labeled by source and vintage, and every neighboring town's number is kept on its own line rather than folded into an average. This is not legal advice.

The Two AirROI Numbers, Kept Separate

AirROI publishes Stevensville data two different ways, and they don't agree with each other closely enough to average. The town-page pull, covering July 2025 through June 2026, puts a typical year at about $65,968 in revenue, 39.6% occupancy, an ADR of $586, and RevPAR of $242, across 77 active listings. The Maryland state table — a separate scrape from the same day — lists Stevensville's row differently: $4,964 per month, which labels out to roughly $59,568 per year, on a sample of 76 listings, 37.9% occupancy, and ADR of $566. That row ranks Stevensville #1 by monthly revenue on Maryland's state table.

Neither number is wrong; they're pulled from different slices of the same underlying data and shouldn't be blended into one figure. The honest read is a range: call it roughly $59,500 to $66,000 for a typical entire-home listing, with occupancy somewhere in the high 30s and ADR in the mid-$500s to upper $500s. A sample size of 76 or 77 listings is real, sourced data, but it's small enough that a handful of standout properties can move the mean — worth saying plainly rather than presenting either figure as gospel.

What both pulls agree on: Entire Home/Apt listings make up 96.1% of the 77 active rentals AirROI tracked, supply grew 13.2% over the prior period, and the typical booking window runs about 84 days out. That last number matters for pricing strategy — Stevensville guests are planning ahead, not booking on a whim three days before a weekend.

The two tables likely differ because they're built from different snapshot windows and different listing sets even on the same scrape date — one anchored to a rolling twelve-month town extract, the other to a cross-market state comparison table that samples Maryland markets side by side. That's a normal quirk of aggregator data, not a red flag about either number's legitimacy. The practical takeaway for a host: don't cherry-pick whichever figure looks better for a pitch deck or a listing valuation. Cite both, label the vintage, and let the range do the honest work.

Where the Money Comes From: The Calendar

Both AirROI pulls point to the same seasonal shape even though the dollar totals differ. Revenue peaks in August, with June and July close behind it — the stretch when Kent Island's marinas fill, the Bay Bridge carries peak beach traffic to Ocean City and Rehoboth, and Kent Narrows restaurants run waitlists on weekends. February shows up as the softest revenue month on the town-page extract, with occupancy bottoming out in January. December rounds out the trough alongside January and February.

That's a summer-bay-peak, winter-trough calendar — not the shoulder-heavy pattern you'd see in a college town or a ski market. A host pricing Stevensville off a generic 'high season / low season' template built for a different kind of destination will misprice both ends: overpricing the winter and underpricing the true peak weekends in July and August.

The 84-day average booking window also says something about who's booking. Guests planning a Kent Island weekend nearly three months out are typically locking in a boat slip, a fishing charter, or a specific summer date around a family gathering — not chasing a last-minute deal. That has direct pricing implications: a Stevensville listing can afford to hold firmer rates on peak summer weekends than a market that fills mostly on short-notice, price-sensitive bookings, because the demand is already committed well before arrival.

The Regulatory Picture AirROI Doesn't Capture

AirROI's own site has, at points, tagged Stevensville with a 'low regulation' label. That badge is stale and shouldn't guide a listing decision. Queen Anne's County passed Ordinance #24-09, effective January 11, 2025, establishing a short-term residential rental framework, and the county began accepting annual zoning certificate applications on October 1, 2025 under that ordinance's provisions. This is not a light-touch market anymore, whatever a third-party data badge says.

The county's published worksheet (updated September 2025) lists a Zoning Certificate fee of $130.00 and a Fire Inspection Fee of $100.00. The certificate is issued for one year, with a county inspection required at initial application and then again every five years — a self-certification affidavit may cover the years in between. Once approved, the certificate number links to the Queen Anne's County Tax Portal for applicable lodging taxes. Fee amounts and inspection cadence should always be confirmed against the live QAC worksheet before a host relies on them for planning, since municipal fee schedules do change.

Stevensville itself is a census-designated place — unincorporated Queen Anne's County, not a town with its own separate government. That makes QAC Planning & Zoning the primary desk for a Stevensville parcel. This is not legal advice; hosts should confirm their specific parcel's zoning and certificate status directly with Queen Anne's County before listing a property.

The inspection cadence is worth planning around, not just budgeting for. A county inspection at initial application, then again every five years, means a host's compliance timeline stretches well beyond a first-year checklist — furnishings, smoke and carbon monoxide detection, egress, and whatever else the fire inspection covers need to stay current for the life of the certificate, not just pass once and get forgotten. Once a certificate is approved, linking it to the Queen Anne's County Tax Portal is the step that keeps lodging tax remittance current; skipping that link is a common way hosts end up out of compliance without realizing it.

Why Chestertown's Numbers Don't Belong Here

Chestertown sits up the Eastern Shore in Kent County, and it operates under an entirely different desk: the Town of Chestertown's Chapter 138 registration requirement for non-owner-occupied short-term rentals, layered on top of Kent County's own tax portal. AirROI's Maryland table lists Chestertown at $3,053 per month, on a sample of 63 listings, 36.4% occupancy, and $387 ADR — a materially different profile from Stevensville's, both in dollar terms and in guest type. Chestertown sells colonial architecture and a walkable historic downtown along the Chester River; Stevensville sells bridge access, marinas, and Bay proximity. Filing Chestertown's regulatory file or revenue year onto a Stevensville property is simply the wrong desk and the wrong comp.

Two other Maryland markets show up in the same conversation and deserve the same separation. Annapolis, per figures cited in this market's planning brief, runs materially under Stevensville's vintage — call that a WATCH figure pending a fresh pull, since it comes from a secondary source rather than a direct AirROI table row. And McHenry, near Deep Creek Lake, posts its own Maryland-table figure that's simply a different kind of Maryland market — a mountain lake destination with nothing in common with a Chesapeake Bay bridge town beyond sharing a state line. None of these towns' numbers should be used to size a Stevensville listing, and none of Stevensville's numbers should be exported to size theirs.

What a Stevensville Host Should Actually Do With This

Treat the roughly $59,500–$66,000 range, the high-30s occupancy, and the mid-$500s to upper-$500s ADR as your planning band, not a promise — then measure your own listing's trailing twelve months against it. A property that's underperforming that range is worth auditing on photos, pricing calendar, and how well the listing actually communicates 'ten minutes from the Bay Bridge, walk to Kent Narrows seafood' rather than generic Eastern Shore copy.

Confirm your zoning certificate status with Queen Anne's County before you assume the AirROI 'low regulation' label still describes your situation — it doesn't, as of Ordinance #24-09. And if you're benchmarking against a neighboring market for any reason, keep the comparison honest: Stevensville, Chestertown, Annapolis, and McHenry are four different Maryland stories with four different guests, four different desks, and four different years.

None of this replaces professional advice specific to your property. A market report can tell you what the aggregate data says and what the county's ordinance requires in general terms; it can't tell you whether your particular parcel qualifies, what your specific tax obligation looks like, or how a lender will read your trailing twelve months. Use this as the starting point for those conversations, not the substitute for them.

What's Actually Driving Demand in This Market

The revenue and occupancy figures don't explain themselves without the geography behind them. Stevensville sits at the western end of Kent Island, right where U.S. 50/301 comes off the Chesapeake Bay Bridge — which means every car headed from the DC/Baltimore/Annapolis corridor to Ocean City or Rehoboth Beach passes through, or near, this town. That bridge-adjacency is a demand driver in its own right, separate from Stevensville's own attractions: beach-bound travelers who'd rather stop for a night on the Bay side than push straight through, and boaters using Kent Narrows' marinas as a home base for a Chesapeake weekend.

That's a genuinely different guest profile from a colonial-tourism destination like Chestertown, where the draw is the town itself — walkable brick streets, historic architecture, a slower pace built around exploring on foot. Stevensville's draw is more transactional and more water-based: proximity to a boat slip, easy bridge access, a jumping-off point rather than a destination to wander. Listings that lean into that — marina distance in the headline, boat trailer parking called out explicitly, a description that name-checks Kent Narrows seafood rather than vague 'charming coastal town' language — tend to match what guests are actually searching for when they type 'Stevensville MD vacation rental' or 'Kent Island Airbnb near the bridge.'

There's a secondary Annapolis-overflow effect worth flagging too. When Annapolis lodging fills or prices out during peak weekends, some travelers headed to the capital region look across the Bay Bridge for a still-convenient alternative — Stevensville sits close enough to make that swap realistic without adding meaningful drive time. That's a smaller slice of demand than the beach-traffic or boater segments, but it's real, and it points toward another reason Stevensville and Annapolis shouldn't be treated as the same market even though they occasionally share the same guest.

Supply Growth and What It Means for a New Listing

13.2% supply growth in a single tracked period is a meaningful jump for a 77-listing market — it means roughly nine or ten new entire-home rentals entered the Stevensville listing stock since the prior count. That's not a saturated market by any stretch, but it's also not the wide-open field it might have looked like two years ago. A new host entering now is competing against a noticeably larger set of listings than the year before, and against properties that have had a full season or more to build reviews and search ranking.

The practical response isn't to avoid the market — the revenue range still supports a healthy entire-home listing — it's to differentiate from day one rather than assume a generic Bay-area listing will find its footing eventually. Photos that show the actual walk to Kent Narrows or the drive time to the Bay Bridge, amenity tags that match what boaters and beach-bound drivers search for, and a calendar priced to the real seasonal curve all matter more in a growing-supply market than they would in a flat one.

It's also worth noting that 96.1% of Stevensville's active supply is Entire Home/Apt listings — private rooms and shared spaces are a rounding error in this market. That concentration tells you what guests expect when they search here: a whole property, likely with parking for a boat trailer or extra vehicles, not a spare bedroom in someone's house. A host considering a private-room product in Stevensville is building against the grain of what the market has trained guests to expect, which doesn't make it impossible, but it does mean pricing and positioning need to work harder to overcome that expectation gap.

Reading This Report Alongside a Purchase or a Repricing Decision

This report is a planning input, not a valuation. If you're sizing a potential purchase, the roughly $59,500–$66,000 revenue range gives you a top-line figure to stress-test against a specific property's bedroom count, walkability to water, and condition — not a number to plug in unadjusted. If you're repricing an existing listing, compare your trailing twelve months against both AirROI figures rather than just the more flattering one, and be honest with yourself about where the gap comes from: calendar strategy, photos, or a listing that still reads like it could be anywhere on the Eastern Shore.

Either way, the county's regulatory posture is no longer a footnote. Ordinance #24-09 changed Stevensville from an aggregator's 'low regulation' badge to a market with an active zoning certificate requirement, a fire inspection, and a tax-portal link. Any revenue projection that doesn't account for that compliance step — cost, timing, and the five-year inspection cycle — is incomplete.

Frequently Asked Questions

How much does an Airbnb make in Stevensville, MD?

AirROI's two pulls put a typical entire-home year between roughly $59,568 and $65,968, depending on which table you're reading — the Maryland state table (n=76) versus the town-page extract (77 listings). Occupancy runs in the high 30s and ADR sits between about $566 and $586. Treat this as a range, not a single figure, and measure your own property's trailing twelve months against it.

Is Stevensville, MD the same market as Chestertown?

No. Stevensville is an unincorporated Kent Island community in Queen Anne's County; Chestertown is an incorporated town in Kent County with its own Chapter 138 short-term rental registration requirement. They have different guests, different desks, and different revenue profiles — Chestertown's AirROI figure runs well under Stevensville's for this vintage.

Does Queen Anne's County require a permit for short-term rentals?

Yes. Ordinance #24-09 took effect January 11, 2025, and the county began accepting annual short-term residential rental zoning certificate applications on October 1, 2025. This is not legal advice — confirm your specific parcel's requirements directly with Queen Anne's County Planning & Zoning.

What does a Queen Anne's County short-term rental permit cost?

The county's worksheet, updated September 2025, lists a Zoning Certificate fee of $130.00 and a Fire Inspection Fee of $100.00, with the certificate valid for one year. Confirm current fees on the live QAC worksheet before budgeting, since municipal fee schedules can change.

When is the slow season for a Stevensville rental?

AirROI's data points to January, February, and December as the softest months, with occupancy bottoming in January and revenue softest in February on the town-page extract. Summer — June through August — carries the peak, with August as the top revenue month.

How many active short-term rental listings does Stevensville have?

AirROI counted 77 active listings on its town-page extract, with Entire Home/Apt properties making up 96.1% of that supply. Supply grew 13.2% over the prior tracked period.

Is Stevensville's occupancy sample size reliable?

AirROI's samples run 76 to 77 listings depending on which table you reference. That's real, sourced data, but it's a small enough sample that outlier properties can shift the average — worth treating as a directional range rather than a precise figure.

What's the difference between Stevensville and Kent Island?

Kent Island is the broader landmass Stevensville sits on, along with the Bay Bridge crossing and Kent Narrows. Stevensville is the main unincorporated community and commercial center on the island — most Kent Island short-term rental activity and guest search terms reference Stevensville, Kent Narrows, or the Bay Bridge directly.

Should I compare Stevensville to Annapolis for pricing?

Not directly. Annapolis is a separate, larger Western Shore market with its own guest base, and the figure cited for it in this market's planning brief runs meaningfully under Stevensville's vintage. rather than blending them.

Where do I confirm current Stevensville short-term rental rules?

Queen Anne's County Planning & Zoning publishes the current short-term residential rental information and worksheet on qac.org. That's the primary desk for Stevensville parcels since Stevensville is unincorporated county land, not its own town government.

Work with Crest & Cove Creative

Marketing a Stevensville stay with regional Eastern Shore stock photos and Chestertown-flavored copy leaves the listing looking like every other Bay-area rental instead of the specific bridge-town it is. Name the failure mode the guest can check on the listing.

A market-fit audit checks whether your listing's photos, copy, and calendar actually match what Stevensville guests search for. Book one before your next pricing update. Send the live listing draft and the facts you can actually cite.

Reach out at crestcove.co or (256) 998-7502.