A homeowner two miles from Wittman Regional Airport called our office this spring with a simple question: could she rent her house out for EAA AirVenture week and pocket the income without dealing with paperwork. The honest answer took longer than she expected, because the answer depends on an address line most people never think about twice.
Oshkosh, for regulatory purposes, is not one place. The City of Oshkosh and the Town of Oshkosh are separate governments with separate short-term rental ordinances, and they draw the line for who needs a permit in almost opposite ways. A homeowner half a mile inside the city limit and a homeowner half a mile outside it can rent an identical house for the identical week and end up under two entirely different sets of rules.
The stakes are easy to see in the numbers from the most recent AirVenture. EAA AirVenture Oshkosh 2026 ran July 20 through 26 at Wittman Regional Airport, marking the 73rd year of the event and tying its "Celebrating the Freedom of Flight" theme to the America250 anniversary. More than 10,000 aircraft and upward of 600,000 attendees passed through the area that week, and every hotel room within driving distance booked out early. It is the one week of the year when a spare bedroom in Oshkosh can outearn a month of long-term rent, which is exactly why the permit question is worth settling before the next one rolls around.
Two Governments, Two Different Trigger Points
The City of Oshkosh's rule is the simpler one to state and the stricter one in practice. According to the city's official short-term rental guidance, anyone renting their home to guests for 28 consecutive days or shorter in a calendar year needs both a Short-Term Rental Permit and a Room Tax permit. There is no minimum-nights exemption built in. Rent your house for a single week during EAA and you have triggered the same permit requirement as someone running a rental business year-round.
The Town of Oshkosh, the separate township that surrounds the city, took a different approach when it adopted its own Short-Term Rental Ordinance on March 24, 2025, effective April 1, 2025. Under that ordinance, a property owner can rent a primary residence as a short-term rental without a license as long as the total is 10 days or less in a year. The town's own guidance on the ordinance addresses the EAA scenario directly, noting that renting a primary residence only during the event would likely fit the 10 days or less exemption.
| City of Oshkosh | Town of Oshkosh | |
|---|---|---|
| Permit trigger | Any rental of 28 days or shorter | More than 10 days per year |
| One EAA week only | Permit and Room Tax required | Likely exempt, no license needed |
| Governing document | City Short-Term Rental FAQ | 2025 ordinance, effective 4/1/2025 |
That single week of AirVenture sits comfortably under the town's 10-day threshold. It sits squarely inside the city's 28-day trigger. The same seven nights of income can be permit-free or permit-required depending entirely on which municipality holds jurisdiction over the parcel.
What The City Actually Asks For
If your property falls inside the City of Oshkosh, renting it out during AirVenture week means filing for the Short-Term Rental Permit through the city's Planning Services office and registering for Room Tax collection, since the city treats any stay of 28 nights or fewer as lodging rather than a private favor between homeowner and guest. There is no carve-out for a single busy week. A homeowner who rents only during EAA, and nothing else all year, still meets the same 28-day-or-shorter definition that applies to someone running short-term rentals every month.
That is worth knowing before you book your first EAA guest, because the permit process and Room Tax registration take time to set up, and AirVenture week does not move to accommodate a slow paperwork season.
What The Town Adds Through The County
Outside the city limit, in the Town of Oshkosh, a homeowner who stays under the 10-day threshold likely avoids the license altogether for an EAA-only rental. But the moment a property crosses into regular short-term rental use, whether through repeat weekend bookings or a non-primary-residence setup, the town's own license fees apply: $200 for new applicants and $100 annually for renewals, with the license period running May 1 through April 30.
There is a second layer that catches people off guard. If the property is not the owner's primary residence and was already operating as a short-term rental before the ordinance took effect, it falls under a grandfather provision, but that provision required applying by May 15, 2025, a deadline that has already passed. Anyone who missed it starts the licensing process fresh rather than carrying over prior operating history.
Any short-term rental operating under a state license also goes through the Winnebago County Health Department as a Tourist Rooming House. First-time applicants pay $212 for the pre-inspection plus $151 for the license itself, a total of $363 up front, with renewals at $151 annually, expiring each June 30. The inspection checks the basics that matter for a week packed with out-of-town guests: smoke detectors, carbon monoxide detectors, stair railings, and general safety code compliance.
Why This Outlasts One Week In July
The boundary question does not disappear after AirVenture ends. It follows the property. A buyer evaluating a house near the EAA grounds for its rental income potential needs to know which side of the city and town line it sits on before assuming a single summer week of rental income comes free of permitting. A seller who has been quietly renting out a spare room during EAA for years, inside the city limit, without a permit, is disclosing an unregistered short-term rental history to any buyer who asks the right question during due diligence.
It also affects how a property gets valued as an income asset. A house in the Town of Oshkosh that can plausibly clear the 10-day exemption for EAA week alone carries a lighter compliance burden than an otherwise identical house two streets over inside the city limit, where the same rental activity requires ongoing Room Tax collection and permit renewal. That is not a cosmetic difference. It is the kind of detail that changes what a buyer actually gets for the price, the same way lake frontage or septic status changes what a waterfront parcel actually delivers.
Before You List Your Address For EAA Week
A few questions worth answering before you accept a single booking:
- Does the parcel sit inside the City of Oshkosh limits or in the surrounding Town of Oshkosh? The address alone will not always tell you. City and county parcel records will.
- If you are inside the city, have you filed for the Short-Term Rental Permit and registered for Room Tax before your first guest arrives?
- If you are in the town and renting only during EAA, have you confirmed your total rental days for the year stay at or under 10?
- If the property is not your primary residence, are you operating under a valid town license, or did you miss the May 15, 2025 grandfather deadline and need to apply fresh?
A Few Quick Questions
Does the short-term rental license transfer when I sell the property? Licenses are tied to the current ordinance holder and the property's use history, not automatically inherited by a new owner. A buyer planning to continue short-term rental use should confirm licensing requirements apply to them directly rather than assuming continuity from the seller.
What if my house sits right on the city and town boundary? Jurisdiction follows the parcel, not the mailing address, so a survey or a call to the county's zoning office is the only reliable way to confirm which ordinance applies.
Do I owe Room Tax either way? Room Tax obligations follow the City of Oshkosh's rules specifically. A property in the Town of Oshkosh operating under the 10-day exemption is not automatically subject to the same Room Tax registration, though anyone unsure should confirm directly with the relevant office before collecting rental income.
Whether you are weighing a first EAA rental or evaluating a property near Wittman Field for its income potential, the permit question is easier to answer before you list than after a guest has already checked in. The team at Better Homes and Gardens Real Estate Special Properties knows this stretch of Winnebago County parcel by parcel, city line by town line. Get the Special Advantage. Talk with our team today.
