Wellfleet, MA Short-Term Rental Market Report 2026

For hosts weighing whether to buy, price, or keep operating a short-term rental in Wellfleet, the numbers below come from AirROI's trailing twelve months, August 2025 through July 2026, across 246 active listings. This is a data snapshot, not a marketing plan or a startup checklist. The goal is to give owners, buyers, and lenders a single, dated read on what the market actually did over the past year, so decisions get made against the real number rather than a peak-week story or a neighboring town's figure mistakenly carried over.

Typical listings earned about $31,996 over the trailing twelve months, at an average nightly rate of $434 and 39.6 percent occupancy. Revenue per available night, the figure that blends rate and occupancy into one number, worked out to $192. Revenue was down 11.5 percent from the prior year. For underwriting purposes, treat $31,996 as the typical host year for a standard Wellfleet listing, not a ceiling, and treat the year-over-year decline as a real signal about market conditions rather than noise.

This report covers what Wellfleet hosts earned, who is operating in this market and at what scale, when the calendar is strong versus soft, where guests are coming from, and what the town's own registration reference says about opening a listing here. Regulatory and tax questions get a brief, clearly labeled mention, but the full sequencing on those belongs to a separate piece built specifically for that purpose; this report exists to establish the numbers, not the compliance steps. This is not legal advice.

What Wellfleet Hosts Earned in 2026

Typical listings earned about $31,996 last year from the 246 active rentals AirROI tracked, on an average nightly rate of $434 and 39.6 percent occupancy. Revenue per available night came in at $192, which is the single figure that best represents blended performance across a full calendar year rather than a peak-week snapshot.

The year-over-year direction matters as much as the level. Revenue was down 11.5 percent from the prior twelve-month period, while active listing supply held essentially flat. That combination means the decline is not explained by more listings splitting a similar total pool of demand; it reflects existing hosts earning less per listing than they did the year before. Anyone modeling next year's numbers off last year's should build that softening into the forecast rather than assuming a rebound to the prior year's figure.

For underwriting purposes, treat $31,996 as the typical host year for a standard Wellfleet listing, not a ceiling and not a floor. A well-positioned, well-reviewed, well-photographed listing can outperform the median, and a listing with pricing or presentation problems can underperform it. But the median is the right starting point for a pro forma, a lender conversation, or a buyer's first-pass math, rather than a best-case month pulled from someone else's marketing copy.

It is also worth being precise about what each figure in this snapshot actually measures, since the terms get used loosely elsewhere. The $31,996 median is annual revenue for a typical active listing, not profit; operating costs, cleaning, taxes, and any management fee come out of that figure separately and are not part of this report. The $434 average nightly rate reflects what booked nights actually charged, blended across the full sample, including both peak-season and off-season bookings. The 39.6 percent occupancy figure is the share of available nights that were actually booked across the full year, again blended across the whole calendar rather than isolated to any single month.

Revenue per available night, at $192, is useful precisely because it combines rate and occupancy into a single comparable figure. Two markets, or two individual listings, can post very different average rates and very different occupancy percentages and still land on a similar revenue-per-available-night figure, which is why this metric is often the more reliable one for comparing performance across properties or across time periods, rather than looking at rate or occupancy in isolation.

Who Is Renting: Inside the 246-Listing Sample

246 active listings is a solid sample for a town Wellfleet's size, large enough to support meaningful averages rather than a handful of outlier properties skewing the whole picture. Within that sample, superhost share is 56.9 percent, meaning more than half of active listings carry that platform designation, and professionally managed share is 27.6 percent, meaning roughly one in four listings is run by a management company rather than the owner directly.

Del Mar Vacations is the largest single operator in the market, with 44 listings, a meaningful share of the total 246 active supply. That concentration is worth noting for two reasons. First, it means a portion of Wellfleet's short-term rental supply is professionally optimized on pricing, photography, and calendar management at a scale an individual owner-operator cannot easily match. Second, it means the remaining supply, still the clear majority of the market, is run by owners and smaller operators who are competing against that professionalized segment without the same tooling or scale advantages.

For a new or prospective host, the practical read is this: more than a quarter of your competitive set is professionally managed, and the market's single largest operator controls close to a fifth of active supply on its own. That is not a reason to avoid the market, but it is a reason to take pricing and presentation seriously rather than assuming an independent listing will automatically compete on equal footing with a professionally managed one.

The superhost figure deserves a similar note of context. A 56.9 percent superhost share means the designation is common rather than rare in this market, which in turn means it functions less as a strong differentiator in a guest's eyes and more as a baseline expectation. A listing without superhost status in a market where more than half the competitive set already carries it is starting from a slightly different position than the same listing would occupy in a market where the designation is scarce.

None of this composition data changes the underlying revenue figures reported above; it explains who is earning them. A market with meaningful professional-management presence and a large anchor operator is a different competitive environment than a market made up entirely of individual owner-operators, even when the headline revenue numbers land in a similar range.

Peak Season: August, July, and June Carry the Year

Wellfleet's short-term rental calendar is heavily front-loaded toward summer. August, July, and June are the three strongest months, with August standing out as the clear peak of the year. That concentration means a large share of the $31,996 typical annual revenue is earned in a relatively narrow window, and the blended $434 average night and 39.6 percent occupancy figures for the full year understate what a well-booked August specifically can look like, and overstate what an average month across the full calendar delivers.

For hosts building a pricing calendar, the practical implication is to treat peak months as their own pricing product rather than a simple percentage markup over a baseline rate. Guests booking August in Wellfleet are choosing a specific, high-demand window months in advance, and pricing that window at a rate disconnected from off-peak months captures value that a flatter, evenly-distributed rate structure leaves on the table.

The concentration also has staffing and turnover implications that a purely revenue-focused read of the numbers can miss. A market that earns most of its year in a two-to-three-month window needs cleaning, maintenance, and guest-communication capacity sized for that peak, not for the calendar's average month, which means the operational cost side of running a Wellfleet listing is also front-loaded even though this report focuses on revenue.

A host who treats the entire non-summer calendar as one undifferentiated off-season, rather than checking month by month, risks underpricing or underpromoting a shoulder month that performs better than the deep winter trough this report identifies separately below.

February Is the Slow Season

February is the slowest month for both occupancy and revenue, consistent with the broader Cape Cod off-season pattern. Demand does not disappear entirely in the winter months, but it drops to a level well below what the annual averages in this report suggest if read without the seasonal context.

Some hosts offset this seasonal trough with extended-stay or remote-worker bookings in winter and early spring, filling calendar nights that would otherwise sit empty at a lower nightly rate in exchange for length of stay and reduced turnover cost. That is a strategy choice each operator has to weigh against their own property and cost structure, but it is a documented pattern in how some hosts in this and comparable Outer Cape markets manage the off-season rather than simply accepting near-zero winter occupancy.

For a buyer or new host modeling cash flow across a full year, February and the surrounding winter months should be modeled as genuinely soft, not as a smaller version of the summer pattern. Treating the whole year as evenly seasonal, or assuming winter simply scales down proportionally from summer, will overstate off-season revenue and understate how concentrated Wellfleet's actual demand is.

This also affects how a buyer should read a seller's trailing-twelve-month statement during due diligence. A statement that shows steady month-over-month revenue with no clear winter trough is either an unusually differentiated property, an unusually aggressive winter pricing and marketing strategy, or a number that deserves closer scrutiny against the pattern this broader market data shows. February softness is the norm here, not the exception, and a listing's own numbers should be read against that baseline.

Where Wellfleet's Guests Come From

Hosts asking where most Wellfleet guests come from get a consistent answer in this data: Boston is the top origin market, followed closely by New York City. Both metros are within a half-day's drive or a short flight of the Outer Cape, which helps explain both the strength of the summer peak and the relatively long booking lead time the market shows, since a drivable or short-flight destination lends itself to advance planning around a specific weekend or week.

For marketing and content decisions that sit outside this report's scope, that origin pattern is useful context: a listing's photography, amenities, and description are being read primarily by guests who already have some familiarity with New England coastal towns and are choosing among several similar options, not by guests unfamiliar with the region who need extensive orientation to the area itself.

This report does not extend into what to do with that guest-origin information in a listing description or ad campaign; that is a marketing question addressed elsewhere. Here, the guest-origin data is presented as one more piece of the underlying market picture, alongside revenue, seasonality, and the composition of who is currently operating in the market.

The Boston-and-New-York concentration also has a practical implication for how a host should read demand signals outside the peak booking window. Both metros carry their own local event calendars, school schedules, and weather patterns that can shift booking timing even when Wellfleet's own conditions haven't changed. A soft week in the booking calendar is sometimes a Wellfleet-specific signal and sometimes a reflection of something happening in the origin markets themselves, and distinguishing between the two is worth the effort before reacting with a price cut.

Registering a Short-Term Rental with the Town

This report is a data snapshot, not a compliance guide, so the registration note here is intentionally brief. Wellfleet references a short-term rental registration process on its town newsflash page, and AirROI's regulation labeling for a market like this is based on a scrape of public listings, not a certified reading of the town code, useful as a signal, not a substitute for calling Town Desk. A dedicated permit fee was not confirmed on a primary town page as of this writing.

Anyone using this report to decide whether to open a listing in Wellfleet should treat the revenue and seasonality figures above as the market picture, and treat the actual registration requirement, fee, and zoning classification for their specific parcel as a separate question to resolve directly with the clerk's office before committing capital. The two questions, what the market pays and what the town requires, are both real and both necessary, but they are answered by different sources and should not be conflated.

Buyers and hosts evaluating this or any comparable market should keep the numbers, the regulatory posture, and any comparison to another town on separate, clearly labeled lines rather than blending them into a single impression of what a coastal New England short-term rental market looks like.

This distinction matters most at the exact moment a buyer is comparing a data aggregator's town-level regulatory tag against an actual purchase decision. A tag describing a market as lightly regulated is a useful first filter for narrowing a search across many towns, but it is not the basis on which to finalize a purchase, set a launch date, or promise a lender a specific opening timeline. Those decisions depend on what the clerk's office says about your specific parcel, on the day you call, not on how a scrape happened to categorize the town months or years earlier.

Don't Blend Wellfleet's Numbers With Vinalhaven's

Vinalhaven, Maine is a separate island market reached primarily by ferry, with a much smaller sample of 43 active listings and a typical host year of $15,718, roughly half of Wellfleet's median. The two markets appear side by side often enough in short-term rental write-ups that it is worth stating plainly: they should never be averaged or cited interchangeably.

Underwrite a Wellfleet property on Wellfleet's own $31,996 median and 246-listing sample, and a Vinalhaven property on its own $15,718 figure and 43-listing sample. Treat them as two distinct markets with separate numbers, separate access patterns, and separate seasonal profiles, not as two data points on the same coastal New England curve.

The practical risk of blending the two is straightforward: a buyer or host who anchors expectations on a blended or averaged figure will misjudge either market, expecting too little from Wellfleet or too much from Vinalhaven. in every conversation, every spreadsheet, and every pro forma where both might come up.

This same discipline applies to any other coastal town that might get mentioned alongside Wellfleet in a broader regional write-up or a portfolio comparison. This report's numbers, the $31,996 median, the 246-listing sample, the seasonal pattern, and the operator composition described above, apply specifically to Wellfleet as measured over this trailing twelve-month window. They should not be extended to a neighboring town, even one with superficial similarities in geography or housing stock, without that town's own dated data behind the claim.

Related Reading

More Wellfleet, Massachusetts reading already live on Crest & Cove.

• Market a Wellfleet Stay: Photograph Cahoon Hollow Beach by Name

• Wellfleet STR Rules: Registering with Town Desk

• Wellfleet Shoulder Season: August Peak, February Hole

• Wellfleet Remote Stays: A 30-Night Minimum Is Not Occupancy

• DIY vs. Hire in Wellfleet: Independent Hosts Still Own This Desk

• Who Books a Wellfleet Rental: Boston First, Then New York

• Buying a Wellfleet Rental: budget 31,996, Not Vinalhaven's Number

• Wellfleet Tourism Data: What Draws Guests Beyond the Beach

• Complete Visitor's Guide to Wellfleet, Massachusetts

• What It Costs to Start a Legal Wellfleet STR in 2026

• Financing a Wellfleet Rental: DSCR Loans Explained

• Wellfleet vs. Vinalhaven STR Desks: Two Coasts, Two Rulebooks

• Wellfleet vs. Vinalhaven: Two Towns, Keep Those Years Apart

Frequently Asked Questions

How much did a typical Wellfleet short-term rental earn over the past year?

Typical listings earned about $31,996 over the trailing twelve months from August 2025 through July 2026, across 246 active rentals tracked by AirROI, at an average nightly rate of $434 and 39.6 percent occupancy. Revenue per available night was $192.

Is the Wellfleet short-term rental market growing or shrinking?

Revenue was down 11.5 percent from the prior year while active supply held essentially flat, meaning existing listings earned less per unit rather than the market simply spreading across more competing properties.

What share of Wellfleet listings are professionally managed?

Professionally managed share is 27.6 percent of the 246-listing sample, and superhost share is 56.9 percent. Del Mar Vacations is the largest single operator in the market, with 44 listings.

When is Wellfleet's peak short-term rental season?

August, July, and June are the three strongest months, with August the clear peak. Most of the market's annual revenue concentrates in that window, so peak pricing should be treated as its own product rather than a simple markup over an annual average rate.

When is the slowest month for Wellfleet short-term rentals?

February is the slowest month for both occupancy and revenue, consistent with the broader Cape Cod off-season. Some hosts use extended-stay or remote-worker bookings to offset the seasonal trough in winter and early spring.

Where do most Wellfleet short-term rental guests come from?

Boston is the top origin market for Wellfleet guests, followed closely by New York City. Both metros are within a half-day's drive or a short flight of the Outer Cape.

Does Wellfleet require short-term rental registration?

Wellfleet references a short-term rental registration process on its town newsflash page. A dedicated permit fee was not confirmed on a primary town page as of this writing, so confirm current requirements and any fee directly with the clerk's office for your specific parcel.

Should I compare Wellfleet's numbers to Vinalhaven, Maine?

No. Vinalhaven is a separate island market reached primarily by ferry, with 43 active listings and a typical host year of $15,718, roughly half of Wellfleet's median. Underwrite each market on its own figures rather than averaging or blending them.

How large is the Wellfleet short-term rental sample this report is based on?

AirROI tracked 246 active Wellfleet listings over the trailing twelve months, August 2025 through July 2026, which is a solid sample size for a town Wellfleet's scale and supports the averages and shares reported here.

What does this report not cover?

This is a data snapshot on revenue, seasonality, guest origin, and market composition. It does not cover listing marketing strategy, startup costs, or the full sequencing of town registration and Massachusetts tax compliance, each of which is a separate topic addressed elsewhere.

Is the average nightly rate the same as what a well-run listing should expect to earn?

The $434 average nightly rate and 39.6 percent occupancy are blended, typical figures across the full 246-listing sample and full year. A well-positioned, well-reviewed listing can outperform this median; it is a starting point for a pro forma, not a guaranteed outcome for any single property.

Work with Crest & Cove Creative

246 listings, one typical year of $31,996, and more than a quarter of the market run by professional operators: here is what Wellfleet's trailing twelve months actually show. Name the failure mode the guest can check on the listing.

Reach out at crestcove.co or (256) 998-7502 to talk through what these numbers mean for your specific Wellfleet listing or acquisition. Name the failure mode the guest can check on the listing. Send the live listing draft and the facts you can actually cite.

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