Winter, WI Airbnb Market Data, Statistics, and Occupancy Rates

Winter Short-Term Rental Market Overview

Winter, Wisconsin is a small, seasonal short-term rental market tucked into the Northwoods with just 21 active Airbnb listings. The market's average daily rate of $283 sits below the $368 state average, and occupancy runs at 17% compared to 38% statewide — hallmarks of a vacation-cabin market with intense summer demand and quiet shoulder seasons. Average annual revenue comes in at $22,222 per listing, making this a market best suited for investors who can keep acquisition costs low and lean into peak-season pricing.

Key Market Statistics

According to Rabbu market data, the Winter short-term rental market shows:

Data sources: Rabbu proprietary analytics as of Apr, 27 2026.

Why Investors Consider Winter

Investors consider Winter for its low-competition environment, affordable property prices relative to lakefront markets, and strong summer demand driven by outdoor recreation.

Expert Market Assessment

"Winter presents a niche opportunity rather than a high-volume investment play. Revenue is heavily concentrated in the summer months — July alone accounts for roughly $4,516 in average monthly revenue, more than four times the annual monthly average — so cash-flow planning needs to account for extended quiet periods in spring and late fall. That said, the tiny supply of just 21 listings means a well-appointed lakefront cabin can capture outsized demand during peak weeks. Investors comfortable with seasonal income patterns and low carrying costs may find this market quietly rewarding."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winter

Average revenue by month in Winter

Winter's revenue is sharply seasonal: July ($4,516) and August ($4,208) together account for nearly 40% of annual earnings, while April ($457) is the weakest month. This roughly 10x spread between peak and trough underscores the importance of maximizing summer pricing and considering minimum-stay strategies to capture full-week bookings.

Active Airbnb listings by property size in Winter

Supply is relatively balanced across the three property sizes tracked, with 7 three-bedroom units, 6 two-bedrooms, and 5 one-bedrooms. The modest total of 18 listings across these categories suggests low competition at every size, though investors targeting family-sized cabins (3 bedrooms) will find the most crowded — albeit still tiny — segment.

Average daily rate (ADR) by property size in Winter

ADR climbs steadily from $137 for 1-bedroom units to $252 for 3-bedroom properties, an 84% premium. The jump from 1 to 2 bedrooms ($137 to $216) is proportionally the largest, suggesting that adding a second bedroom significantly expands the guest pool and rate ceiling.

Average RevPAN by property size in Winter

Three-bedroom properties lead with a RevPAN of $47, more than double the $20 figure for 1-bedroom units. This gap indicates that larger cabins not only command higher nightly rates but also convert available nights into revenue more efficiently, making them the strongest performers on a per-night basis.

Average occupancy rates by property size in Winter

Occupancy rates are low across all sizes — 15% for 1-bedrooms, 14% for 2-bedrooms, and 19% for 3-bedrooms — reflecting the market's deep seasonality. Three-bedroom units edge ahead, likely because families and groups booking summer lake trips fill these properties more consistently during peak weeks.

Average monthly revenue by property size in Winter

Monthly revenue ranges from $604 for 1-bedroom listings up to $1,711 for 3-bedroom properties, nearly a 3x difference. Two-bedroom units land at $1,530, making the incremental revenue gain from a second to third bedroom relatively modest compared to the jump from one to two bedrooms.

Average annual revenue by property size in Winter

Three-bedroom properties generate an average of $20,537 per year, followed by 2-bedrooms at $18,364 and 1-bedrooms at just $7,255. Investors targeting the strongest return potential should focus on 3-bedroom cabins, though 2-bedroom units offer a competitive alternative with slightly lower acquisition and upkeep costs.

Most common amenities for Airbnb listings in Winter

Parking and a full kitchen are universal at 100% of listings, while self check-in (91%), a backyard (86%), and outdoor furniture (71%) round out the top five — all pointing to a self-sufficient cabin experience guests expect in the Northwoods. Lake access appears in 52% of listings and waterfront in 48%, signaling that water proximity is a meaningful differentiator rather than a given, and investors who secure lakefront properties can stand out.

Short-Term Rental Regulations in Winter

Understanding local STR regulations is essential before investing in Winter. Here's the current regulatory landscape:

Permit Requirements

Short-term rental operators in Winter, Wisconsin may need to obtain a tourist rooming house license from the state and should verify whether Sawyer County or the Town of Winter imposes additional registration or permitting requirements. Investors are encouraged to check directly with local authorities before listing a property.

Key Restrictions

Common restrictions that may apply include occupancy limits tied to bedroom count, minimum-night stay requirements, noise and quiet-hour ordinances, parking capacity rules, and any HOA or lake-association covenants that govern rental activity. Given the rural, lake-focused nature of the area, septic capacity and dock usage rules are also worth confirming.

Tax Obligations

Wisconsin imposes a state sales tax and a room tax on short-term rental stays, and Sawyer County may levy an additional local room tax. Major booking platforms typically collect and remit state-level taxes, but hosts should confirm local tax obligations are covered as well.

Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Winter can provide current regulatory guidance.

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, expect Winter's revenue pattern to remain sharply seasonal, with July and August continuing to drive the bulk of annual income. ADR could edge up modestly — perhaps 1–3% — as remote-work travelers and outdoor recreation enthusiasts continue discovering Wisconsin's lake country, though occupancy gains are likely to be incremental given the area's cold-weather off-season. Investors should build financial plans that assume significant revenue concentration in the June-through-September window, with winter snowmobile and ice-fishing traffic providing a smaller secondary boost."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winter, WI

What is the average Airbnb occupancy rate in Winter?

The average occupancy rate for Airbnb listings in Winter, WI is currently 17%, which is well below the Wisconsin state average of 38%. This reflects the market's highly seasonal nature — demand surges in summer and drops significantly during shoulder and off-peak months. Properties with lake access or waterfront positioning tend to perform better during the peak window.

How much do Airbnb hosts make in Winter?

On average, Airbnb hosts in Winter earn approximately $1,851 per month and $22,222 per year based on trailing 12-month booking data. Revenue varies significantly by property size: 1-bedroom listings average around $7,255 annually, while 3-bedroom properties bring in roughly $20,537. Peak summer months like July can generate over $4,500 in a single month.

Is Winter a good market for Airbnb investment?

Winter can work well for investors who secure properties at low acquisition costs and are comfortable with seasonal cash flow. The market has very limited competition with only 21 active listings, and 3-bedroom cabins deliver the strongest returns at about $20,537 per year. The key is managing expectations around off-season income and maximizing revenue during the June-through-September peak.

What is the average daily rate (ADR) for Airbnb in Winter?

The average daily rate in Winter is $283, which falls below the Wisconsin state average of $368. ADR scales with property size: 1-bedroom units average $137, 2-bedrooms come in at $216, and 3-bedroom properties command $252 per night. These rates reflect the rural, cabin-style inventory that characterizes this Northwoods market.

Are short-term rentals legal in Winter?

Short-term rentals are generally permitted in Winter, WI, though operators may need to secure a Wisconsin tourist rooming house license and comply with any local regulations from Sawyer County or the Town of Winter. Specific rules around occupancy limits, septic capacity, and lake-use restrictions may also apply. It's always best to verify current requirements with local authorities before listing a property.

When is peak season for Airbnb in Winter?

Peak season in Winter runs from June through August, with July being the strongest month at an average of $4,516 in revenue. August follows closely at $4,208. A secondary bump occurs in September and October as fall foliage draws visitors, while February sees a modest winter-activity boost to $1,391. April is the softest month, averaging just $457.

How many Airbnbs are there in Winter?

As of April 2026, there are 21 active Airbnb listings in Winter, WI. The supply breaks down fairly evenly across sizes: 5 one-bedroom units, 6 two-bedroom properties, and 7 three-bedroom listings. This small inventory means competition is limited, which can benefit well-positioned properties during peak demand periods.

How is Airbnb revenue calculated in Winter?

The annual and monthly revenue figures for Winter are derived from the trailing 12 months of historical booking performance for active comparable Airbnb listings in the market — not a forward-looking projection. We average each comparable listing's actual revenue per available night (RevPAN) by month over the past year, drop regional outliers, and roll the remainder up to a market-level historical average. This anchors the figures to what hosts have actually earned recently rather than to forecasts, while still naturally reflecting seasonal peaks and slower months because each month uses its own historical performance. Individual results can vary based on property quality, pricing strategy, and operational management.

About Rabbu Market Data

Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.

What this data includes

• Regularly updated active Airbnb and STR listing counts for the Winter, WI market
• Average daily rate, occupancy, and RevPAN metrics broken down by property size
• Monthly and annual revenue trends based on trailing 12-month booking performance
• Popular amenity prevalence across active listings to benchmark guest expectations
• Data sourced from Rabbu proprietary analytics and combined for consistency

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages as of April 2026 and may not capture very recent market shifts. Local regulations, HOA rules, and seasonal conditions can significantly affect individual property performance.