Town of Winchester, Wisconsin Airbnb Market Data 2026: STR Report & Statistics
How much can you earn on Airbnb in Town of Winchester, Wisconsin? Based on AirROI's 2026 dataset (April 2025 – March 2026), the short answer is $26,527 per year — at a $326 nightly rate, 34.0% occupancy, and a $117 RevPAR that reflects moderate rate-to-revenue efficiency with room to optimize.
With just 29 active listings, Town of Winchester is a micro-market where selective demand that rewards strong listing quality and pricing strategy. Supply expanded 141.7% as revenue climbed even while nightly rates softened — occupancy gains are outrunning rate pressure. For hosts entering now, strengthening demand means there is still room to build a profitable listing.
Regulation is low with minimal registration requirements, pointing to an operator-friendly environment. In a market this size, differentiated listings with strong reviews can capture outsized returns relative to the competition.
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What Are the Key Airbnb Metrics in Town of Winchester?
In Town of Winchester, the headline Airbnb metrics are $26,527 in average annual revenue,34.0% occupancy, $326 ADR, and $117 in RevPAR, and guests book about 77 days in advance.
How Much Do Airbnb Hosts Earn Monthly in Town of Winchester?
Understanding the monthly revenue variations for Airbnb listings in Town of Winchester is key to maximizing your short term rental income potential. Seasonality significantly impacts earnings. Our analysis, based on data from the past 12 months, shows that the peak revenue month for STRs in Town of Winchester is typically July, while March often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Town of Winchester across different performance tiers:
- Best-in-class properties (Top 10%) achieve $6,615+ monthly, often utilizing dynamic pricing and superior guest experiences.
- Strong performing properties (Top 25%) earn $4,346 or more, indicating effective management and desirable locations/amenities.
- Typical properties (Median) generate around $2,615 per month, representing the average market performance.
- Entry-level properties (Bottom 25%) see earnings around $1,347, often with potential for optimization.
Average Monthly Airbnb Earnings Trend in Town of Winchester
What Is the Monthly Airbnb Occupancy Rate in Town of Winchester?
Maximize your bookings by understanding the Town of Winchester STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Augustsees the highest demand (peak season occupancy), while March experiences the lowest (low season). Effective strategies, like adjusting minimum stays or offering promotions, can boost occupancy during slower periods. Here's how different property tiers perform in Town of Winchester:
- Best-in-class properties (Top 10%) achieve 61%+ occupancy, indicating high desirability and potentially optimized availability.
- Strong performing properties (Top 25%) maintain 42% or higher occupancy, suggesting good market fit and guest satisfaction.
- Typical properties (Median) have an occupancy rate around 28%.
- Entry-level properties (Bottom 25%) average 16% occupancy, potentially facing higher vacancy.
Average Monthly Occupancy Rate Trend in Town of Winchester
What Is the Average Airbnb Nightly Rate in Town of Winchester?
Effective short term rental pricing strategy in Town of Winchester involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Town of Winchester typically peaks in July and dips lowest during November. Leveraging Airbnb dynamic pricing tools or strategies based on this seasonality can significantly boost revenue. Here's a look at the typical nightly rates achieved:
- Best-in-class properties (Top 10%) command rates of $573+ per night, often due to premium features or locations.
- Strong performing properties (Top 25%) achieve nightly rates of $430 or more.
- Typical properties (Median) charge around $310 per night.
- Entry-level properties (Bottom 25%) earn around $221 per night.
Average Daily Rate (ADR) Trend by Month in Town of Winchester
What Is the RevPAR for Airbnb in Town of Winchester?
RevPAR in Town of Winchester is currently $117. Because RevPAR combines nightly rates with realized occupancy, it is one of the cleanest ways to compare how efficiently listings turn demand into revenue across the market.
- Entry-level properties (Bottom 25%) see $59 RevPAR.
- Typical properties (Median) generate $123 RevPAR.
- Strong performers (Top 25%) earn $173 RevPAR.
- Best-in-class (Top 10%) achieve $190 RevPAR.
Average Monthly RevPAR Trend in Town of Winchester
RevPAR Insights for Town of Winchester
- The average RevPAR in Town of Winchester is $117. This metric combines nightly rates with realized occupancy, making it one of the best single-number indicators of market efficiency.
- The gap between the top 10% ($190) and bottom 25% ($59) is $132, indicating significant performance disparity driven by property quality, pricing strategy, and location.
- RevPAR peaks in Jul and bottoms out in Mar, mirroring the broader seasonal demand pattern and suggesting opportunities for dynamic pricing.
Recommendations for Hosts
- Track your own RevPAR monthly against these Town of Winchester benchmarks. If your RevPAR falls below the median of $123, examine whether low occupancy or low ADR is the primary drag.
- Top-quartile listings achieve $173+ RevPAR through a combination of competitive pricing, strong reviews, and strategic amenities. Target this tier through incremental improvements.
- Use RevPAR rather than revenue alone when comparing properties of different sizes — it normalizes for available nights and gives a more accurate picture of performance.
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When Is the Peak Season for Airbnb in Town of Winchester?
Town of Winchester's peak Airbnb season falls in July, August, June, while the softest stretch is March, April, November. Overall, the market shows highly seasonal trends requiring careful strategy, which should guide pricing, minimum stays, and cash-flow planning.
Peak Season (July, August, June)
- Revenue averages $6,384 per month
- Occupancy rates average 55.1%
- Daily rates average $426
Shoulder Season
- Revenue averages $2,386 per month
- Occupancy maintains around 24.0%
- Daily rates hold near $384
Low Season (March, April, November)
- Revenue drops to average $1,524 per month
- Occupancy decreases to average 19.5%
- Daily rates adjust to average $361
Seasonality Insights for Town of Winchester
- Airbnb seasonality in Town of Winchester is pronounced. Revenue swings sharply between peak and low months, which means pricing strategy, minimum-stay settings, and cash reserves all need to account for extended slower periods.
- During the high season, the absolute peak month showcases Town of Winchester's highest earning potential, with monthly revenues climbing to $7,439, occupancy reaching 61.4%, and ADRs peaking at $436.
- Conversely, the slowest single month marks the market's lowest point — revenue may dip to $934, occupancy could drop to 14.7%, and ADRs may adjust to $358.
- Lower occupancy paired with meaningful seasonality means hosts in Town of Winchester need to maximize every peak-season booking and seriously consider whether off-season pricing adjustments or minimum-stay changes can capture incremental revenue.
Seasonal Strategies for Maximizing Profit
- Peak Season: Maximize revenue through premium pricing and potentially longer minimum stays. Ensure high availability and consider tightening cancellation policies to reduce last-minute gaps.
- Low Season: Offer competitive pricing, extended-stay discounts, and flexible cancellation policies. Target off-season travelers like remote workers, budget-conscious guests, and travelers with flexible schedules.
- Shoulder Seasons: Implement dynamic pricing that bridges peak and low rates. Target weekend travelers, local events, and business visitors. Slightly more flexible terms than peak season can help maintain occupancy without deep discounting.
- In a highly seasonal market like Town of Winchester, building a cash reserve during the top months is essential for covering fixed costs during the slow period. Automated pricing tools can help capture demand shifts in real time.
Do You Need a License for Airbnb in Town of Winchester?
Low regulation and minimal registration activity in Town of Winchester, Wisconsin, United States point to an operator-friendly environment. That said, even low-regulation markets may have tax collection requirements, safety standards, or HOA rules that affect short-term rental operations. Always verify the latest short-term rental regulations and Airbnb license requirements directly with local government authorities for Town of Winchester to ensure full compliance before hosting.
(Source: AirROI data, 2026, finding no licensed listings among those analyzed)
What Are the Best Neighborhoods for Airbnb in Town of Winchester?
With a compact short-term rental market, Town of Winchester gives early-mover hosts an advantage in the right neighborhoods. The areas listed below are where guest demand and local attractions converge — a useful lens for investors evaluating whether to enter this market and where to position their listing.
| Neighborhood / Area | Why Host Here? (Target Guests & Appeal) | Key Attractions & Landmarks |
|---|---|---|
| Lake Nokomis | A popular destination for nature lovers and outdoor enthusiasts, Lake Nokomis offers scenic views and recreational activities such as fishing, kayaking, and hiking. Ideal for hosts looking to attract families and adventure seekers. | Lake Nokomis Beach, Nokomis Park, Fishing and boating opportunities, Walking trails, Picnic areas |
| Winchester Town Park | A central hub for community events and gatherings, Winchester Town Park is perfect for attracting visitors during local festivals and activities. Great for hosts targeting families and groups attending events. | Winchester Town Park, Local festivals and community gatherings, Playground, Walking paths |
| Northwoods Trails | Known for its extensive hiking and biking trails, the Northwoods area attracts outdoor enthusiasts and nature lovers. Ideal for hosts seeking to cater to adventure tourists and nature retreats. | Hiking and biking trails, Wildlife viewing, Scenic nature spots |
| Cranberry Lake | A beautiful natural lake that offers fishing, swimming, and tranquil scenery. Perfect for hosts who want to provide a peaceful lakeside retreat for their guests. | Cranberry Lake, Boating and fishing, Campsites, Nature photography opportunities |
| Winchester Historical Society | Rich in local history, this area attracts history buffs and tourists interested in the cultural heritage of the region. Great for hosts providing educational experiences. | Historical exhibits, Community events, Local history tours |
| Camp 2 Lake | A serene camping and recreational area, Camp 2 Lake is popular among families and groups looking for a rustic experience. Ideal for hosts targeting outdoor camping enthusiasts. | Campground, Fishing and swimming, Nature trails |
| Boulder Junction | Just a short drive away, this charming town is known for its outdoor activities and friendly community. Ideal for hosts looking to attract tourists seeking a small-town experience with close access to nature. | Shopping and dining, Nearby lakes and forests, Outdoor activities |
| Sandy Beach | A scenic beach area that draws visitors in the summer for swimming and relaxation. Perfect for potential hosts seeking to attract summer vacationers. | Sandy Beach, Swimming, Picnic areas, Family-friendly activities |
With 8 distinct neighborhoods showing meaningful short-term rental activity, Town of Winchester offers diversification within a single market. Investors can tailor their strategy — from high-turnover tourist zones to quieter residential areas that attract longer stays and remote workers.
What Types of Properties Are on Airbnb in Town of Winchester?
Room Type Distribution
Property Type Distribution
Market Composition Insights for Town of Winchester
- The Town of Winchester Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 100% of the 29 active rentals. This indicates strong guest preference for privacy and space.
- Looking at the property type distribution in Town of Winchester, Outdoor/Unique properties are the most common (58.6%), reflecting the local real estate landscape.
- Houses represent a significant 41.4% portion, catering likely to families or larger groups.
Town of Winchester Airbnb Room Capacity Analysis (2026): Bedroom Distribution
Distribution of Listings by Number of Bedrooms
Room Capacity Insights for Town of Winchester
- The dominant room capacity in Town of Winchester is 3 bedrooms listings, making up 31% of the market. This suggests a strong demand for properties suitable for families or small groups.
- Together, 3 bedrooms and 4 bedrooms properties represent 55.1% of the active Airbnb listings in Town of Winchester, indicating a high concentration in these sizes.
- A significant 65.4% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Town of Winchester.
Town of Winchester Vacation Rental Guest Capacity Trends (2026)
Distribution of Listings by Guest Capacity
Guest Capacity Insights for Town of Winchester
- The most common guest capacity trend in Town of Winchester vacation rentals is listings accommodating 8+ guests (41.4%). This suggests the primary traveler segment is likely larger groups.
- Properties designed for 8+ guests and 6 guests dominate the Town of Winchester STR market, accounting for 79.3% of listings.
- 82.7% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Town of Winchester.
- On average, properties in Town of Winchester are equipped to host 6.4 guests.
How Do Listings in Town of Winchester Compare on Quality?
Listing quality in Town of Winchester can be approximated through presentation depth, bedroom count, and how often hosts disclose exact locations. These signals show how professionally the local supply base is merchandised.
Listing Quality Insights for Town of Winchester
- At 38.6 photos per listing on average, Town of Winchester hosts invest well in visual presentation. Listings with 20+ photos consistently outperform in search ranking and conversion.
- 31.0% of listings show their exact location. Lower disclosure rates can increase booking hesitation — guests want to know exactly where they are staying.
Recommendations for Hosts
- Enable exact location if possible — it removes a common source of guest uncertainty and can improve your listing's position in map-based searches.
- Use these quality indicators as a self-audit checklist. Listings that exceed the Town of Winchester averages across all three metrics are better positioned for premium pricing.
What Amenities Do Airbnb Guests Expect in Town of Winchester?
Amenity Prevalence
Amenity Insights for Town of Winchester
- Essential amenities in Town of Winchester that guests expect include: Free parking on premises, TV, Heating, Smoke alarm, Wifi, Kitchen, Refrigerator, Bed linens, Stove, Fire pit. Lacking these (any) could significantly impact bookings.
Recommendations for Hosts
- Ensure your listing includes all essential amenities for Town of Winchester: Free parking on premises, TV, Heating, Smoke alarm, Wifi, Kitchen, Refrigerator, Bed linens, Stove, Fire pit.
- Prioritize adding missing essentials: Free parking on premises, TV, Heating, Refrigerator, Bed linens, Stove, Fire pit.
- Highlight unique or less common amenities you offer (e.g., hot tub, dedicated workspace, EV charger) in your listing description and photos.
- Regularly check competitor amenities in Town of Winchester to stay competitive.
Which Airbnb Amenities Boost Revenue in Town of Winchester?
Not every amenity matters equally. This table focuses on the amenities most associated with higher revenue in Town of Winchester, which makes it more useful for prioritizing upgrades than a simple popularity list alone.
| Amenity | Prevalence | Revenue With | Revenue Without | Revenue Uplift |
|---|---|---|---|---|
Dishwasher | 51.7% | $33,501 | $19,056 | 75.8% |
Boat slip | 58.6% | $32,279 | $18,379 | 75.6% |
Air conditioning | 62.1% | $31,414 | $18,532 | 69.5% |
Washer | 55.2% | $32,281 | $19,446 | 66.0% |
Coffee | 24.1% | $37,891 | $22,912 | 65.4% |
Dryer | 51.7% | $32,548 | $20,076 | 62.1% |
Luggage dropoff allowed | 41.4% | $33,138 | $21,861 | 51.6% |
Free street parking | 17.2% | $36,502 | $24,449 | 49.3% |
Clothing storage | 72.4% | $29,181 | $19,560 | 49.2% |
Exterior security cameras on property | 31.0% | $33,982 | $23,173 | 46.6% |
Revenue Impact Insights for Town of Winchester
- Dishwasher tops the revenue impact list with a 75.8% uplift — listings with this amenity earn $33,501 vs. $19,056 without it.
Recommendations for Hosts
- Focus your upgrade budget on amenities in the top half of this table. Below-median amenities may improve guest experience but contribute less to revenue growth.
- Highlight revenue-impacting amenities prominently in your listing title, photos, and description — guests can't value what they don't notice.
Dive Deeper: Advanced Town of Winchester STR Market Data (2026)
Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Town of Winchester. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.
Explore Advanced MetricsTown of Winchester Airbnb Guest Demographics & Profile Analysis (2026)
Guest Profile Summary for Town of Winchester
- The typical guest profile for Airbnb in Town of Winchester consists of primarily domestic travelers (97%), often arriving from nearby Madison, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
- Domestic travelers account for 96.9% of guests.
- Key international markets include United States (96.9%) and DC (2.1%).
- Top languages spoken are English (83.3%) followed by Spanish (11.1%).
- A significant demographic segment is the Post-2000s (Gen Z/Alpha) group, representing 50% of guests.
Recommendations for Hosts
- Target domestic marketing efforts towards travelers from Madison and Milwaukee.
- Tailor amenities and listing descriptions to appeal to the dominant Post-2000s (Gen Z/Alpha) demographic (e.g., highlight fast WiFi, smart home features, local guides).
- Highlight unique local experiences or amenities relevant to the primary guest profile.
- Consider seasonal promotions aligned with peak travel times for key origin markets.
What Are Airbnb Guest Ratings in Town of Winchester?
Listings in Town of Winchester average 4.86 out of 5 overall, with about 18.9 reviews per active listing and 41.4% of listings carrying the Guest Favorite badge.
Rating Breakdown by Category
Guest Rating Insights for Town of Winchester
- With an overall rating of 4.86, Town of Winchester listings meet an exceptionally high bar. Guests consistently report strong satisfaction, which drives repeat bookings and referral traffic.
- The strongest subcategory is Check-in (4.94), while Value (4.71) trails behind — a useful signal for hosts looking to prioritize upgrades.
- 41.4% of listings carry the Guest Favorite badge, a strong trust signal that can meaningfully lift click-through and booking rates.
Recommendations for Hosts
- Focus improvement efforts on Value — even small gains in the weakest subcategory can lift overall ratings and search ranking.
- Encourage guests to leave reviews after checkout. Listings with more reviews rank higher in search results and convert browsers into bookers more effectively.
Town of Winchester Airbnb Booking Patterns (2026): Available vs. Booked Days
Available Days Distribution
Booked Days Distribution
Booking Pattern Insights for Town of Winchester
- The most common availability pattern in Town of Winchester falls within the 271-366 days range, representing 69% of listings. This suggests many properties have significant open periods on their calendars.
- Approximately 100.0% of listings show high availability (181+ days open annually), indicating potential for increased bookings or specific owner usage patterns.
- For booked days, the 31-90 days range is most frequent in Town of Winchester (51.7%), reflecting common guest stay durations or potential owner blocking patterns.
How Far in Advance Do Guests Book Airbnb in Town of Winchester?
Average Booking Lead Time by Month
Booking Lead Time Insights for Town of Winchester
- The overall average booking lead time for vacation rentals in Town of Winchester is 77 days.
- Guests book furthest in advance for stays during July (average 142 days), likely coinciding with peak travel demand or local events.
- The shortest booking windows occur for stays in April (average 4 days), indicating more last-minute travel plans during this time.
- Seasonally, Summer (114 days avg.) sees the longest lead times, while Spring (38 days avg.) has the shortest, reflecting typical travel planning cycles.
Recommendations for Hosts
- Use the overall average lead time (77 days) as a baseline for your pricing and availability strategy in Town of Winchester.
- For July stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 142 days out to capitalize on advance planning.
- During April, focus on last-minute booking availability and promotions, as guests book with very short notice (4 days avg.).
- Target marketing efforts for the Summer season well in advance (at least 114 days) to capture early planners.
- Monitor your own booking lead times against these Town of Winchester averages to identify opportunities for dynamic pricing adjustments.
What Is the Average Length of Stay for Airbnb in Town of Winchester?
Guests in Town of Winchester stay about 4.9 nights on average, generating roughly 408 reservations and 14.1 bookings per listing in the latest AirROI dataset. The most common check-in time is 4:00 PM and check-out is 10:00 AM.
Monthly Length of Stay in Town of Winchester
Check-in Time Distribution
Check-out Time Distribution
Stay Pattern Insights for Town of Winchester
- A mid-range stay length points to leisure-driven demand — weekend getaways and short vacations. Hosts should optimize for quick turnover efficiency while keeping the guest experience smooth.
- 14.1 bookings per listing is a manageable pace that balances revenue with operational overhead.
- Stay lengths peak in Jul (6.1 nights) and shorten in Jan (3 nights). Adjust minimum-night requirements seasonally to match.
Recommendations for Hosts
- With shorter average stays, focus on streamlining turnover. Self-check-in, reliable cleaning crews, and pre-staged amenities can reduce per-booking operational costs.
- Set your check-in time to match or beat the market standard of 4:00 PM. Offering early check-in flexibility can be a low-cost differentiator.
- Monitor length-of-stay seasonality to adjust minimum-night requirements — longer minimums during peak periods maximize revenue while shorter minimums fill gaps in shoulder seasons.
Town of Winchester Airbnb Minimum Stay Requirements Analysis
Distribution of Listings by Minimum Night Requirement
2 Nights
10 listings
34.5% of total
3 Nights
2 listings
6.9% of total
4-6 Nights
6 listings
20.7% of total
7-29 Nights
2 listings
6.9% of total
30+ Nights
9 listings
31% of total
Key Insights
- The most prevalent minimum stay requirement in Town of Winchester is 2 Nights, adopted by 34.5% of listings. This highlights the market's preference for shorter, flexible bookings.
- A significant segment (31%) caters to monthly stays (30+ nights) in Town of Winchester, pointing to opportunities in the extended-stay market.
Recommendations
- Align with the market by considering a 2 Nights minimum stay, as 34.5% of Town of Winchester hosts use this setting.
- A 2-night minimum appears standard (34.5%). Consider this for weekends or peak periods.
- Explore offering discounts for stays of 30+ nights to attract the 31% of the market seeking extended stays.
- Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Town of Winchester.
Town of Winchester Airbnb Cancellation Policy Trends Analysis (2026)
Super Strict 30 Days
2 listings
6.9% of total
Flexible
2 listings
6.9% of total
Moderate
2 listings
6.9% of total
Firm
21 listings
72.4% of total
Strict
2 listings
6.9% of total
Cancellation Policy Insights for Town of Winchester
- The prevailing Airbnb cancellation policy trend in Town of Winchester is Firm, used by 72.4% of listings.
- A majority (79.3%) of hosts in Town of Winchester utilize Firm or Strict policies, indicating a market where hosts prioritize booking security.
- Strict cancellation policies are quite rare (6.9%), potentially making listings with this policy less competitive unless justified by high demand or property type.
Recommendations for Hosts
- Consider adopting a Firm policy to align with the 72.4% market standard in Town of Winchester.
- Using a Strict policy might deter some guests, as only 6.9% of listings use it. Evaluate if potential revenue protection outweighs possible lower booking rates.
- Regularly review your cancellation policy against competitors and market demand shifts in Town of Winchester.
How Much Are Airbnb Cleaning Fees in Town of Winchester?
Cleaning fees in Town of Winchester are meaningful operating levers, not just pass-through charges. What matters most is how often hosts charge them, how high they run relative to market norms, and how large a share of gross revenue they consume.
Cleaning Fee Insights for Town of Winchester
- 93.1% of listings charge a cleaning fee, making it standard practice in Town of Winchester. Guests expect it and factor it into their booking decisions.
- The average cleaning fee of $235 is close to the median ($250), suggesting a relatively consistent fee structure across the market.
- Cleaning fees represent 13.2% of gross revenue on average — a significant line item that impacts total guest cost and competitiveness.
Recommendations for Hosts
- Price your cleaning fee competitively against the Town of Winchester median of $250. Fees significantly above market norms can deter bookings, especially for shorter stays.
- Consider whether bundling the cleaning fee into a slightly higher nightly rate might improve conversion, since many guests filter by total price and separate fees can feel punitive.
- Monitor competitor cleaning fees regularly. Airbnb's search algorithm factors in total price, so a well-calibrated cleaning fee can improve your listing's ranking.
What Do the Top Airbnb Listings in Town of Winchester Look Like?
Benchmark your potential! Explore examples of top-performing Airbnb properties in Town of Winchesterbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.
Waterfront Resort | Sleeps 18 | 5 Separate Units
Entire Place • 5 bedrooms
ON Water Lodge! 5 Beds!
Entire Place • 4 bedrooms
Dock Hollands
Entire Place • 3 bedrooms
Cozy Northwoods Cabin Getaway!
Entire Place • 4 bedrooms
Sticks and Stones on the Lake
Entire Place • 4 bedrooms
The Northwoods At It's Finest!
Entire Place • 3 bedrooms
Note: Performance varies based on location, size, amenities, seasonality, and management quality. Data reflects the past 12 months.
Who Are the Top Airbnb Hosts in Town of Winchester?
Learn from the best! This table showcases top-performing Airbnb hosts in Town of Winchester based on the number of properties managed and estimated total revenue over the past year. Analyze their scale and performance metrics.
| Host Name | Properties | Grossing Revenue | Stay Reviews | Avg Rating |
|---|---|---|---|---|
| Bear Country | 11 | $317,067 | 121 | 4.87/5.0 |
| Lindsey | 1 | $53,053 | 37 | 4.95/5.0 |
| Nathan | 1 | $51,642 | 56 | 4.88/5.0 |
| Mark | 1 | $51,600 | 46 | 4.96/5.0 |
| Darren | 1 | $43,930 | 10 | 5.00/5.0 |
| David | 1 | $40,649 | 9 | 4.78/5.0 |
| Kristin | 1 | $35,064 | 53 | 4.98/5.0 |
| Peter | 1 | $30,378 | 17 | 5.00/5.0 |
| Laura | 1 | $29,052 | 24 | 4.92/5.0 |
| Andrea | 1 | $28,266 | 13 | 5.00/5.0 |
Analyzing the strategies of top hosts, such as their property selection, pricing, and guest communication, can offer valuable lessons for optimizing your own Airbnb operations in Town of Winchester.
Who Are the Airbnb Hosts in Town of Winchester?
Town of Winchester is a quality-focused market, with a high Superhost share and fairly mature operating standards.
Host Profile Insights for Town of Winchester
- With 69.0% Superhosts, Town of Winchester has an experienced host base that sets high guest expectations. New entrants should plan for competitive quality standards.
- 17.2% of listings are professionally managed, reflecting a market still dominated by individual hosts.
- 0.0% of listings have Instant Book enabled. Lower Instant Book adoption means many guests must request approval, which can slow conversions.
- 75.9% of listings use Airbnb's simplified pricing (host-only fee), where the host pays the entire platform service fee and the guest sees one all-in price with no separate Airbnb service charge. High adoption signals a professional, PMS-connected host base — Airbnb mandates simplified pricing for software-connected listings.
Recommendations for Hosts
- Consider enabling Instant Book — it reduces booking friction and Airbnb's algorithm tends to favor Instant Book listings in search results.
- With 37.9% cohosted listings, there may be a growing local market for property management services.
- Benchmark your host metrics against these Town of Winchester averages regularly and adjust your hosting strategy based on what top performers do differently.
Top Professional Management Companies in Town of Winchester
These are the highest-grossing professional property management operations in Town of Winchester, ranked by total revenue across their portfolio. Their performance metrics offer a benchmark for what institutional-level hosting looks like in this market.
| Company | Listings | Revenue | ADR | Occ. | Rating |
|---|---|---|---|---|---|
| Bear Country | 11 | $317,067 | $291 | 33.6% | 4.87/5 |
| David | 1 | $40,649 | $481 | 39.7% | 4.78/5 |
| Laura | 1 | $29,052 | $338 | 58.1% | 4.92/5 |
| Vacasa Wisconsin | 2 | $7,116 | $495 | 11.4% | 4.29/5 |
Management Company Insights for Town of Winchester
- The leading management company, Bear Country, operates 11 listings with $317,067 in gross revenue — a useful benchmark for what scale looks like in Town of Winchester.
- Top managers average 4 properties each, suggesting professional management in Town of Winchester still operates at a relatively boutique scale.
- Professionally managed listings in the top tier average 4.72/5 in guest ratings — demonstrating that scale and quality can coexist.
Recommendations
- With only 17.2% of listings professionally managed, there may be an opportunity to differentiate through more structured operations and consistent guest experiences.
- Study how top management companies price, position, and maintain their portfolios — their ADR and occupancy rates reflect strategies refined across dozens of listings.
- If you're considering hiring a property manager, compare their portfolio performance against these benchmarks before committing.
How Does Town of Winchester's Airbnb Market Compare to Nearby Cities?
How does the Town of Winchester Airbnb market stack up against its neighbors? Compare key performance metrics like average monthly revenue, ADR, and occupancy rates in surrounding areas to understand the broader regional STR landscape.
Compared with Tofte Township, Town of Winchester has 14 percentage points lower occupancy and about $15 higher ADR. That helps frame whether this market is winning more on demand, pricing, or both.
| Market | Active Properties | Monthly Revenue | Daily Rate | Avg. Occupancy |
|---|---|---|---|---|
| Schroeder Township | 10 | $5,266 | $420.14 | 40% |
| Lutsen | 22 | $5,131 | $441.97 | 45% |
| Schroeder | 10 | $5,005 | $487.50 | 46% |
| Tofte Township | 44 | $4,650 | $311.61 | 48% |
| Allouez Township | 16 | $4,593 | $367.31 | 46% |
| West Cook | 123 | $4,371 | $374.67 | 46% |
| Lutsen Township | 172 | $4,223 | $445.98 | 37% |
| Grand Marais | 71 | $3,781 | $308.32 | 47% |
| Town of Scott | 23 | $3,685 | $342.80 | 39% |
| Republic Township | 17 | $3,631 | $308.17 | 43% |
Frequently Asked Questions About Airbnb in Town of Winchester
These quick answers summarize the most common investor and operator questions using AirROI's latest market data for Town of Winchester.
How much do Airbnb hosts make in Town of Winchester?
Town of Winchester hosts earn about $26,527 per year on average, with an average nightly rate of $326 and RevPAR of $117. Those figures describe the typical revenue environment for active listings in Town of Winchester, Wisconsin, not the ceiling for the best operators. Source: AirROI 2026 data, Town of Winchester market, April 2025 to March 2026.
What is the average Airbnb occupancy rate in Town of Winchester?
The average Airbnb occupancy rate in Town of Winchester is 34.0%. July is the strongest month and March is the softest, so hosts should expect demand to move meaningfully throughout the year rather than stay flat.
What is the average Airbnb daily rate in Town of Winchester?
Listings in Town of Winchester average $326 per night. The broader pricing spread also matters: lower-performing listings cluster closer to the lower quartiles, while premium homes can price materially above the city average when demand spikes or listing quality stands out.
How many Airbnb listings are active in Town of Winchester?
Town of Winchester currently has about 29 active Airbnb listings in AirROI's market dataset. That supply count helps explain how competitive the market is, how much depth there is for benchmarking, and whether the market behaves like a niche destination or a scaled urban market.
How strict are short-term rental regulations in Town of Winchester?
AirROI currently classifies the short-term rental regulation level in Town of Winchester as Low. The dataset also shows about 0.0% of listings with registration evidence. That is a market signal, not legal advice, so hosts should still confirm current licensing and compliance rules locally before listing.
What is the RevPAR for Airbnb in Town of Winchester?
RevPAR in Town of Winchester is about $117. That metric combines pricing and occupancy into one efficiency number, so it is often a better quick benchmark than ADR alone when investors want to compare how well listings convert nightly rates into realized revenue.
Is Airbnb profitable in Town of Winchester?
Occupancy of 34.0% means Town of Winchester is a more selective market. Profitability is achievable but requires careful cost management, premium positioning, or targeting longer stays to reduce turnover. Average annual revenue is $26,527, but individual returns depend on property type, location within the city, and the host's operating efficiency.
How far in advance do guests book Airbnb in Town of Winchester?
The average booking lead time in Town of Winchester is about 77 days — a longer planning horizon typical of destination or vacation markets where travelers book well in advance. Hosts who understand their market's booking cadence can adjust minimum stays and pricing windows accordingly.
What are the best neighborhoods for Airbnb in Town of Winchester?
Based on AirROI's analysis, some of the top neighborhoods for short-term rentals in Town of Winchester include Lake Nokomis, Winchester Town Park, Northwoods Trails. Each area attracts different guest profiles — from business travelers to leisure visitors — so the best location depends on the property type and target audience a host is aiming for. See the full neighborhood breakdown above.
What type of property performs best on Airbnb in Town of Winchester?
entire_home listings make up 100.0% of the active supply in Town of Winchester. The most common configuration does not always mean the most profitable — operators who identify underserved property types or bedroom counts can sometimes outperform the market average by filling a gap in local supply.
How does Town of Winchester compare to nearby Airbnb markets?
Among neighboring markets, Schroeder Township posts $63,190 in average annual revenue with 39.5% occupancy, compared to Town of Winchester's $26,527 and 34.0%. Comparing nearby markets helps investors understand whether a destination's performance reflects local demand or broader regional trends.
What is the average length of stay in Town of Winchester?
The average Airbnb stay length in Town of Winchester is about 4.9 nights. That matters for turnover, cleaning operations, and pricing strategy because shorter stays increase changeovers while longer stays can smooth occupancy and reduce operational friction.
What is the average Airbnb guest rating in Town of Winchester?
Airbnb listings in Town of Winchester average 4.86 out of 5 overall. About 41.4% of listings carry the guest favorite badge, which suggests a meaningful share of inventory is competing on review quality rather than price alone.
Which amenities boost Airbnb revenue in Town of Winchester?
Dishwasher and Boat slip are among the strongest revenue-linked amenities in Town of Winchester. In AirROI's latest dataset, listings with these amenities outperform those without on average revenue, which makes amenities analysis useful for prioritizing investment and listing upgrades.
Do Airbnb hosts charge cleaning fees in Town of Winchester?
Yes. About 93.1% of active Airbnb listings in Town of Winchester charge a cleaning fee, and the average fee is $235. The more important operating benchmark is how much of gross revenue that fee consumes, not just the absolute dollar amount.
What percentage of Airbnb hosts are Superhosts in Town of Winchester?
A 69.0% Superhost rate signals a highly competitive market where review quality and responsiveness are table stakes, not differentiators.
About AirROI Market Data
AirROI tracks over 20 million properties across 190+ countries and maintains 15+ years of historical performance data, making it one of the deepest Airbnb and STR intelligence platforms available. The analytics pipeline aggregates listing-level data monthly — revenue, occupancy, nightly rates, RevPAR, guest demographics, booking patterns, and competitive supply — so investors and operators can benchmark any market against its own history and against neighboring destinations.
Real estate investors, property managers, financial institutions, hedge funds, tourism boards, hospitality consultants, tech platforms, and academic researchers rely on AirROI data to underwrite acquisitions, optimize pricing, model macro trends, and conduct peer-reviewed research. Data is available through in-depth market reports like this one and the Airbnb API with 22 endpoints and an Airbnb MCP Server for AI agents.
AirROI proprietary analytics as of 2026-03-31. Metrics reflect trailing twelve-month aggregates from active listings. Revenue figures are market averages, not projections. Neighborhood descriptions are AI-generated and reviewed for accuracy. For full methodology, see the data methodology page.