Windsor, Capitol Planning Region Airbnb Market Data 2026: STR Report & Statistics
How much can you earn on Airbnb in Windsor, Capitol Planning Region? Based on AirROI's 2026 dataset (April 2025 – March 2026), the short answer is $16,923 per year — at a $184 nightly rate, 38.7% occupancy, and a $73 RevPAR that reflects moderate rate-to-revenue efficiency with room to optimize.
With just 27 active listings, Windsor is a micro-market where moderate demand with room for well-positioned listings to outperform. Supply grew 125.0% over the past year, yet revenue and nightly rates both trended upward — a signal that traveler demand is outpacing new inventory rather than being diluted by it. For hosts, pricing power remains intact even as competition increases.
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 Windsor?
In Windsor, the headline Airbnb metrics are $16,923 in average annual revenue,38.7% occupancy, $184 ADR, and $73 in RevPAR, and guests book about 40 days in advance.
How Much Do Airbnb Hosts Earn Monthly in Windsor?
Understanding the monthly revenue variations for Airbnb listings in Windsor 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 Windsor is typically October, while February often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Windsor across different performance tiers:
- Best-in-class properties (Top 10%) achieve $5,120+ monthly, often utilizing dynamic pricing and superior guest experiences.
- Strong performing properties (Top 25%) earn $3,413 or more, indicating effective management and desirable locations/amenities.
- Typical properties (Median) generate around $1,833 per month, representing the average market performance.
- Entry-level properties (Bottom 25%) see earnings around $706, often with potential for optimization.
Average Monthly Airbnb Earnings Trend in Windsor
What Is the Monthly Airbnb Occupancy Rate in Windsor?
Maximize your bookings by understanding the Windsor STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Octobersees the highest demand (peak season occupancy), while February 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 Windsor:
- Best-in-class properties (Top 10%) achieve 71%+ occupancy, indicating high desirability and potentially optimized availability.
- Strong performing properties (Top 25%) maintain 59% or higher occupancy, suggesting good market fit and guest satisfaction.
- Typical properties (Median) have an occupancy rate around 34%.
- Entry-level properties (Bottom 25%) average 18% occupancy, potentially facing higher vacancy.
Average Monthly Occupancy Rate Trend in Windsor
What Is the Average Airbnb Nightly Rate in Windsor?
Effective short term rental pricing strategy in Windsor involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Windsor typically peaks in November and dips lowest during April. 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 $314+ per night, often due to premium features or locations.
- Strong performing properties (Top 25%) achieve nightly rates of $185 or more.
- Typical properties (Median) charge around $138 per night.
- Entry-level properties (Bottom 25%) earn around $111 per night.
Average Daily Rate (ADR) Trend by Month in Windsor
What Is the RevPAR for Airbnb in Windsor?
RevPAR in Windsor is currently $73. 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 $26 RevPAR.
- Typical properties (Median) generate $58 RevPAR.
- Strong performers (Top 25%) earn $98 RevPAR.
- Best-in-class (Top 10%) achieve $170 RevPAR.
Average Monthly RevPAR Trend in Windsor
RevPAR Insights for Windsor
- The average RevPAR in Windsor is $73. 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% ($170) and bottom 25% ($26) is $143, indicating significant performance disparity driven by property quality, pricing strategy, and location.
- RevPAR peaks in Oct and bottoms out in Feb, mirroring the broader seasonal demand pattern and suggesting opportunities for dynamic pricing.
Recommendations for Hosts
- Track your own RevPAR monthly against these Windsor benchmarks. If your RevPAR falls below the median of $58, examine whether low occupancy or low ADR is the primary drag.
- Top-quartile listings achieve $98+ 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 Windsor?
Windsor's peak Airbnb season falls in October, November, August, while the softest stretch is January, February, March. Overall, the market shows highly seasonal trends requiring careful strategy, which should guide pricing, minimum stays, and cash-flow planning.
Peak Season (October, November, August)
- Revenue averages $3,148 per month
- Occupancy rates average 42.7%
- Daily rates average $178
Shoulder Season
- Revenue averages $2,374 per month
- Occupancy maintains around 42.5%
- Daily rates hold near $166
Low Season (January, February, March)
- Revenue drops to average $1,443 per month
- Occupancy decreases to average 26.4%
- Daily rates adjust to average $159
Seasonality Insights for Windsor
- Airbnb seasonality in Windsor 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 Windsor's highest earning potential, with monthly revenues climbing to $3,529, occupancy reaching 47.9%, and ADRs peaking at $192.
- Conversely, the slowest single month marks the market's lowest point — revenue may dip to $1,257, occupancy could drop to 23.9%, and ADRs may adjust to $153.
- Lower occupancy paired with meaningful seasonality means hosts in Windsor 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 Windsor, 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 Windsor?
Low regulation and minimal registration activity in Windsor, Capitol Planning Region, 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 Windsor to ensure full compliance before hosting.
(Source: AirROI data, 2026, based on 4% licensed listings)
What Are the Best Neighborhoods for Airbnb in Windsor?
With a compact short-term rental market, Windsor 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 |
|---|---|---|
| Downtown Windsor | Vibrant urban area with a mix of culture, dining, and entertainment. Popular among tourists for events and festivals. | Windsor Sculpture Park, The Art Gallery of Windsor, Devonshire Mall, Windsor International Film Festival, Caesars Windsor |
| Walkerville | Historic neighborhood known for its charming architecture and proximity to downtown. Attracts visitors interested in history and the local brewery scene. | Willistead Manor, Walkerville Brewery, Hiram Walker Distillery, The Wyandotte, St. Mary’s Church |
| Riverside | Scenic neighborhood along the Detroit River, known for its parks and beautiful views. Ideal for families and outdoor enthusiasts. | Riverside Park, Pumpkin Park, Dieppe Park, The Detroit Riverwalk, The Windsor Riverfront |
| South Windsor | Residential area with easy access to amenities and attractions. Often sought after by families and longer-term visitors. | Sandwich Brewing Company, Windsor Crossing Premium Outlets, Heritage Park, Adie Knox Herman Community Centre, The Windsor Mosque |
| East Windsor | Growing area known for its diverse community and proximity to shopping centers. Attractive for budget travelers and families. | The Town Centre Plaza, Devonshire Mall, Little River Corridor, Windsor International Airport, Eastside Mario's |
| LaSalle | Suburban neighborhood offering a relaxed atmosphere and close-knit community. Suitable for visitors seeking a peaceful retreat outside the city. | Lasalle Civic Centre, Heritage Park, Lakeside Park, The LaSalle Historical Society, Maranatha Park |
| Tecumseh | Charming small town with a close-knit community feel. Ideal for visitors looking to experience local culture and small-town life. | Lakewood Park, Tecumseh Town Hall, Leslie McCurdy's 'The Spirit of Harriet Tubman', Tecumseh Historical Museum, The Tecumseh Park |
| Old Walkerville | Quaint and picturesque neighborhood known for its unique shops and eateries. Draws visitors interested in local culture and craftsmanship. | Walkerville Brewery, Willistead Manor, Artisan shops and galleries, Parks and river views, Historic architecture |
With 8 distinct neighborhoods showing meaningful short-term rental activity, Windsor 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 Windsor?
Room Type Distribution
Property Type Distribution
Market Composition Insights for Windsor
- The Windsor Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 74.1% of the 27 active rentals. This indicates strong guest preference for privacy and space.
- Looking at the property type distribution in Windsor, House properties are the most common (59.3%), reflecting the local real estate landscape.
- Houses represent a significant 59.3% portion, catering likely to families or larger groups.
- The presence of 18.5% Hotel/Boutique listings indicates integration with traditional hospitality.
- Smaller segments like others, outdoor/unique (combined 7.4%) offer potential for unique stay experiences.
Windsor Airbnb Room Capacity Analysis (2026): Bedroom Distribution
Distribution of Listings by Number of Bedrooms
Room Capacity Insights for Windsor
- The dominant room capacity in Windsor is 2 bedrooms listings, making up 48.1% of the market. This suggests a strong demand for properties suitable for couples or solo travelers.
- Together, 2 bedrooms and 3 bedrooms properties represent 66.6% of the active Airbnb listings in Windsor, indicating a high concentration in these sizes.
- A significant 25.9% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Windsor.
Windsor Vacation Rental Guest Capacity Trends (2026)
Distribution of Listings by Guest Capacity
Guest Capacity Insights for Windsor
- The most common guest capacity trend in Windsor vacation rentals is listings accommodating 4 guests (37%). This suggests the primary traveler segment is likely small families or groups.
- Properties designed for 4 guests and 8+ guests dominate the Windsor STR market, accounting for 51.8% of listings.
- 29.6% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Windsor.
- On average, properties in Windsor are equipped to host 4.1 guests.
How Do Listings in Windsor Compare on Quality?
Listing quality in Windsor 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 Windsor
- At 27.4 photos per listing on average, Windsor hosts invest well in visual presentation. Listings with 20+ photos consistently outperform in search ranking and conversion.
- 14.8% 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 Windsor averages across all three metrics are better positioned for premium pricing.
What Amenities Do Airbnb Guests Expect in Windsor?
Amenity Prevalence
Amenity Insights for Windsor
- Essential amenities in Windsor that guests expect include: Heating, Air conditioning, Smoke alarm, Wifi. Lacking these (any) could significantly impact bookings.
- Popular amenities like Dedicated workspace, Fire extinguisher, Free parking on premises are common but not universal. Offering these can provide a competitive edge.
Recommendations for Hosts
- Ensure your listing includes all essential amenities for Windsor: Heating, Air conditioning, Smoke alarm, Wifi.
- Prioritize adding missing essentials: Heating, Air conditioning.
- Consider adding popular differentiators like Dedicated workspace or Fire extinguisher to increase appeal.
- 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 Windsor to stay competitive.
Which Airbnb Amenities Boost Revenue in Windsor?
Not every amenity matters equally. This table focuses on the amenities most associated with higher revenue in Windsor, which makes it more useful for prioritizing upgrades than a simple popularity list alone.
| Amenity | Prevalence | Revenue With | Revenue Without | Revenue Uplift |
|---|---|---|---|---|
Dining table | 48.1% | $26,514 | $8,018 | 230.7% |
Kitchen | 74.1% | $20,482 | $6,756 | 203.2% |
Private entrance | 51.9% | $24,251 | $9,033 | 168.5% |
Toaster | 59.3% | $22,085 | $9,416 | 134.6% |
Cooking basics | 66.7% | $20,911 | $8,949 | 133.7% |
Clothing storage | 63.0% | $21,130 | $9,773 | 116.2% |
Backyard | 66.7% | $20,514 | $9,742 | 110.6% |
Freezer | 51.9% | $22,602 | $10,808 | 109.1% |
Room-darkening shades | 40.7% | $23,886 | $12,137 | 96.8% |
Dishwasher | 59.3% | $21,094 | $10,857 | 94.3% |
Revenue Impact Insights for Windsor
- Dining table tops the revenue impact list with a 230.7% uplift — listings with this amenity earn $26,514 vs. $8,018 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 Windsor STR Market Data (2026)
Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Windsor. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.
Explore Advanced MetricsWindsor Airbnb Guest Demographics & Profile Analysis (2026)
Guest Profile Summary for Windsor
- The typical guest profile for Airbnb in Windsor consists of primarily domestic travelers (95%), often arriving from nearby New York, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
- Domestic travelers account for 94.8% of guests.
- Key international markets include United States (94.8%) and Canada (1.7%).
- Top languages spoken are English (62.3%) followed by Spanish (19.5%).
- 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 New York and Philadelphia.
- 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 Windsor?
Listings in Windsor average 4.73 out of 5 overall, with about 41.5 reviews per active listing and 33.3% of listings carrying the Guest Favorite badge.
Rating Breakdown by Category
Guest Rating Insights for Windsor
- An average rating of 4.73 places Windsor in solid territory. Most guests leave satisfied, though there is room for hosts to push toward the top tier.
- The strongest subcategory is Communication (4.85), while Value (4.67) trails behind — a useful signal for hosts looking to prioritize upgrades.
- 33.3% 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.
Windsor Airbnb Booking Patterns (2026): Available vs. Booked Days
Available Days Distribution
Booked Days Distribution
Booking Pattern Insights for Windsor
- The most common availability pattern in Windsor falls within the 271-366 days range, representing 66.7% of listings. This suggests many properties have significant open periods on their calendars.
- Approximately 88.9% of listings show high availability (181+ days open annually), indicating potential for increased bookings or specific owner usage patterns.
- For booked days, the 1-30 days range is most frequent in Windsor (33.3%), reflecting common guest stay durations or potential owner blocking patterns.
- A notable 18.5% of properties secure long booking periods (181+ days booked per year), highlighting successful long-term rental strategies or significant owner usage.
How Far in Advance Do Guests Book Airbnb in Windsor?
Average Booking Lead Time by Month
Booking Lead Time Insights for Windsor
- The overall average booking lead time for vacation rentals in Windsor is 40 days.
- Guests book furthest in advance for stays during May (average 58 days), likely coinciding with peak travel demand or local events.
- The shortest booking windows occur for stays in March (average 10 days), indicating more last-minute travel plans during this time.
- Seasonally, Fall (50 days avg.) sees the longest lead times, while Spring (31 days avg.) has the shortest, reflecting typical travel planning cycles.
Recommendations for Hosts
- Use the overall average lead time (40 days) as a baseline for your pricing and availability strategy in Windsor.
- For May stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 58 days out to capitalize on advance planning.
- During March, focus on last-minute booking availability and promotions, as guests book with very short notice (10 days avg.).
- Target marketing efforts for the Fall season well in advance (at least 50 days) to capture early planners.
- Monitor your own booking lead times against these Windsor averages to identify opportunities for dynamic pricing adjustments.
What Is the Average Length of Stay for Airbnb in Windsor?
Guests in Windsor stay about 5.3 nights on average, generating roughly 488 reservations and 18.1 bookings per listing in the latest AirROI dataset. The most common check-in time is 3:00 PM and check-out is 11:00 AM.
Monthly Length of Stay in Windsor
Check-in Time Distribution
Check-out Time Distribution
Stay Pattern Insights for Windsor
- 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.
- 18.1 bookings per listing is a manageable pace that balances revenue with operational overhead.
- Stay lengths peak in Apr (6.3 nights) and shorten in Jan (2.4 nights). Adjust minimum-night requirements seasonally to match.
Recommendations for Hosts
- Leverage the longer-stay pattern by offering weekly discounts — even 5-10% off can convert browsing into bookings for guests considering an extended stay.
- Set your check-in time to match or beat the market standard of 3:00 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.
Windsor Airbnb Minimum Stay Requirements Analysis
Distribution of Listings by Minimum Night Requirement
1 Night
9 listings
33.3% of total
2 Nights
8 listings
29.6% of total
3 Nights
2 listings
7.4% of total
7-29 Nights
1 listings
3.7% of total
30+ Nights
7 listings
25.9% of total
Key Insights
- The most prevalent minimum stay requirement in Windsor is 1 Night, adopted by 33.3% of listings. This highlights the market's preference for shorter, flexible bookings.
- A strong majority (62.9%) of the Windsor Airbnb data shows acceptance of very short stays (1-2 nights), indicating a dynamic, high-turnover market.
- A significant segment (25.9%) caters to monthly stays (30+ nights) in Windsor, pointing to opportunities in the extended-stay market.
Recommendations
- Align with the market by considering a 1 Night minimum stay, as 33.3% of Windsor hosts use this setting.
- Explore offering discounts for stays of 30+ nights to attract the 25.9% of the market seeking extended stays.
- Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Windsor.
Windsor Airbnb Cancellation Policy Trends Analysis (2026)
Super Strict 60 Days
1 listings
3.7% of total
Flexible
10 listings
37% of total
Moderate
9 listings
33.3% of total
Firm
5 listings
18.5% of total
Strict
2 listings
7.4% of total
Cancellation Policy Insights for Windsor
- The prevailing Airbnb cancellation policy trend in Windsor is Flexible, used by 37% of listings.
- The market strongly favors guest-friendly terms, with 70.3% of listings offering Flexible or Moderate policies. This suggests guests in Windsor may expect booking flexibility.
- Strict cancellation policies are quite rare (7.4%), potentially making listings with this policy less competitive unless justified by high demand or property type.
Recommendations for Hosts
- Consider adopting a Flexible policy to align with the 37% market standard in Windsor.
- Using a Strict policy might deter some guests, as only 7.4% 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 Windsor.
How Much Are Airbnb Cleaning Fees in Windsor?
Cleaning fees in Windsor 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 Windsor
- 74.1% of listings charge a cleaning fee, making it standard practice in Windsor. Guests expect it and factor it into their booking decisions.
- The gap between the average ($462) and median ($85) cleaning fee indicates some high-end properties are pulling the average up considerably.
- Cleaning fees represent 10.9% 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 Windsor median of $85. 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 Windsor Look Like?
Benchmark your potential! Explore examples of top-performing Airbnb properties in Windsorbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.
By The River
Entire Place • 5 bedrooms
Relax By The Water
Entire Place • 2 bedrooms
Quiet Comfy Getaway 3 BDR home
Entire Place • 3 bedrooms
Island Vibes
Entire Place • 3 bedrooms
Vintage Windsor Home: Private Yard & Covered Deck
Entire Place • 3 bedrooms
NEW: Spacious Quaint & Convenient Hideaway!
Entire Place • 2 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 Windsor?
Learn from the best! This table showcases top-performing Airbnb hosts in Windsor 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 |
|---|---|---|---|---|
| Grand Slam LLC | 1 | $74,516 | 64 | 4.97/5.0 |
| Bryan | 1 | $57,126 | 66 | 4.97/5.0 |
| Drene | 1 | $48,869 | 96 | 4.93/5.0 |
| Jacqueline | 1 | $40,086 | 94 | 4.90/5.0 |
| Evolve | 1 | $31,145 | 20 | 4.25/5.0 |
| Sandra | 3 | $26,892 | 42 | 4.96/5.0 |
| Natasha | 1 | $22,123 | 45 | 4.76/5.0 |
| Diamond | 4 | $22,088 | 11 | 4.33/5.0 |
| Events With Elegance | 1 | $21,339 | 5 | 5.00/5.0 |
| Claude | 2 | $19,392 | 102 | 4.75/5.0 |
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 Windsor.
Who Are the Airbnb Hosts in Windsor?
Windsor has a relatively balanced host base.
Host Profile Insights for Windsor
- A 40.7% Superhost share is healthy — enough experienced operators to anchor quality without making the market impenetrable for newcomers.
- 3.7% of listings are professionally managed, reflecting a market still dominated by individual hosts.
- 29.6% of listings have Instant Book enabled. Lower Instant Book adoption means many guests must request approval, which can slow conversions.
- 51.9% 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
- Earning Superhost status can significantly improve search ranking and guest trust. Focus on maintaining high response rates, low cancellations, and strong reviews.
- Consider enabling Instant Book — it reduces booking friction and Airbnb's algorithm tends to favor Instant Book listings in search results.
- With 25.9% cohosted listings, there may be a growing local market for property management services.
- Benchmark your host metrics against these Windsor averages regularly and adjust your hosting strategy based on what top performers do differently.
Top Professional Management Companies in Windsor
These are the highest-grossing professional property management operations in Windsor, 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 |
|---|---|---|---|---|---|
| Evolve | 1 | $31,145 | $185 | 50.3% | 4.25/5 |
Management Company Insights for Windsor
- The leading management company, Evolve, operates 1 listings with $31,145 in gross revenue — a useful benchmark for what scale looks like in Windsor.
- Top managers average 1 properties each, suggesting professional management in Windsor still operates at a relatively boutique scale.
- Professionally managed listings in the top tier average 4.25/5 in guest ratings — suggesting room for quality improvement even among larger operators.
Recommendations
- With only 3.7% 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 Windsor's Airbnb Market Compare to Nearby Cities?
How does the Windsor 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 Wellesley, Windsor has 10 percentage points lower occupancy and about $363 lower ADR. That helps frame whether this market is winning more on demand, pricing, or both.
| Market | Active Properties | Monthly Revenue | Daily Rate | Avg. Occupancy |
|---|---|---|---|---|
| Sag Harbor | 15 | $6,214 | $1281.77 | 40% |
| Town of Ancram | 20 | $6,037 | $540.01 | 38% |
| Town of East Hampton | 1,298 | $5,936 | $1031.25 | 35% |
| Middletown | 395 | $5,624 | $614.86 | 44% |
| Town of Southampton | 1,183 | $5,535 | $1042.68 | 33% |
| Monterey | 39 | $5,492 | $465.09 | 44% |
| Town of Pleasant Valley | 26 | $5,430 | $555.79 | 40% |
| Wellesley | 21 | $5,292 | $546.38 | 49% |
| New Shoreham | 120 | $5,232 | $662.43 | 44% |
| North Andover | 12 | $5,229 | $454.46 | 44% |
Frequently Asked Questions About Airbnb in Windsor
These quick answers summarize the most common investor and operator questions using AirROI's latest market data for Windsor.
How much do Airbnb hosts make in Windsor?
Windsor hosts earn about $16,923 per year on average, with an average nightly rate of $184 and RevPAR of $73. Those figures describe the typical revenue environment for active listings in Windsor, Capitol Planning Region, not the ceiling for the best operators. Source: AirROI 2026 data, Windsor market, April 2025 to March 2026.
What is the average Airbnb occupancy rate in Windsor?
The average Airbnb occupancy rate in Windsor is 38.7%. October is the strongest month and February 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 Windsor?
Listings in Windsor average $184 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 Windsor?
Windsor currently has about 27 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 Windsor?
AirROI currently classifies the short-term rental regulation level in Windsor as Low. The dataset also shows about 3.7% 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 Windsor?
RevPAR in Windsor is about $73. 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 Windsor?
Occupancy of 38.7% means Windsor 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 $16,923, 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 Windsor?
The average booking lead time in Windsor is about 40 days — a moderate lead time that gives hosts planning visibility while still benefiting from last-minute bookings. Hosts who understand their market's booking cadence can adjust minimum stays and pricing windows accordingly.
What are the best neighborhoods for Airbnb in Windsor?
Based on AirROI's analysis, some of the top neighborhoods for short-term rentals in Windsor include Downtown Windsor, Walkerville, Riverside. 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 Windsor?
entire_home listings make up 74.1% of the active supply in Windsor. 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 Windsor compare to nearby Airbnb markets?
Among neighboring markets, Sag Harbor posts $74,562 in average annual revenue with 39.7% occupancy, compared to Windsor's $16,923 and 38.7%. 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 Windsor?
The average Airbnb stay length in Windsor is about 5.3 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 Windsor?
Airbnb listings in Windsor average 4.73 out of 5 overall. About 33.3% 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 Windsor?
Dining table and Kitchen are among the strongest revenue-linked amenities in Windsor. 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 Windsor?
Yes. About 74.1% of active Airbnb listings in Windsor charge a cleaning fee, and the average fee is $462. 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 Windsor?
A 40.7% 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.