Winchester, KY Airbnb Market Data, Statistics, and Occupancy Rates

Winchester Short-Term Rental Market Overview

Winchester, KY is a small but evolving short-term rental market with just 20 active Airbnb listings and an average annual revenue of $18,629 per property. With an ADR of $139—well below the Kentucky state average of $333—and occupancy sitting at 26%, the market rewards investors who can source deals at the right price point. Year-over-year listing growth of 188% signals rising investor interest, though the limited supply base means a few new entrants can significantly shift dynamics.

Key Market Statistics

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

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.

Why Investors Consider Winchester

Winchester appeals to investors seeking low-barrier entry in a Kentucky market where favorable supply/demand balance offsets softer occupancy and growth metrics.

Expert Market Assessment

"Winchester represents a competitive opportunity where selective deal sourcing matters more than in higher-volume markets. The ROI score of 51 out of 100 reflects average revenue-to-price fundamentals offset by below-average occupancy stability and growth trends, though a favorable supply/demand balance keeps the door open for well-positioned properties. Seasonality is pronounced: October stands out as the peak month at $2,765 in average revenue, while January and February dip below $650, creating meaningful cash-flow swings. Investors who can secure properties at or below the average home value and target the two-bedroom segment—where annual revenue reaches nearly $30K—will be best positioned to make the numbers work."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winchester

Average revenue by month in Winchester

Winchester's revenue peaks sharply in October at $2,765—nearly five times the January low of $597—revealing significant seasonality that investors must plan around. The April-through-November stretch consistently delivers $1,674 or more, while December through February represents a pronounced soft season.

Active Airbnb listings by property size in Winchester

The market's 20 listings skew heavily toward smaller properties, with 9 one-bedroom and 6 two-bedroom units comprising the tracked supply. The absence of larger three- or four-bedroom listings could signal an underserved niche for investors willing to offer group-friendly accommodations.

Average daily rate (ADR) by property size in Winchester

ADR nearly doubles from $96 for one-bedroom properties to $169 for two-bedrooms, reflecting a strong per-bedroom pricing premium. The jump suggests guests in Winchester are willing to pay substantially more for additional space, making the two-bedroom configuration an attractive proposition from a rate standpoint.

Average RevPAN by property size in Winchester

One-bedroom listings lead in RevPAN at $36 versus $30 for two-bedrooms, driven by their significantly higher occupancy rates. While two-bedrooms command higher nightly rates, one-bedrooms convert more available nights into revenue, making them the more efficient earner on a per-night basis.

Average occupancy rates by property size in Winchester

One-bedroom properties maintain a 38% occupancy rate—more than double the 18% rate for two-bedrooms—indicating steadier demand for smaller, more affordable accommodations. The low two-bedroom occupancy suggests that while those units earn more per booking, filling them consistently remains a challenge in this small market.

Average monthly revenue by property size in Winchester

Despite lower occupancy, two-bedroom listings generate $2,495 per month on average—nearly 85% more than the $1,348 earned by one-bedrooms. The higher ADR of two-bedroom units more than compensates for fewer booked nights, making them the top monthly revenue earners in Winchester.

Average annual revenue by property size in Winchester

Two-bedroom properties lead annual revenue at $29,950, compared to $16,184 for one-bedrooms, representing an 85% premium that could justify the higher acquisition and furnishing costs. Investors targeting the two-bedroom segment should weigh this revenue upside against the lower occupancy stability when underwriting deals.

Most common amenities for Airbnb listings in Winchester

Parking is universal at 100% of listings, followed by kitchens (90%) and self check-in (85%), establishing these as baseline guest expectations in Winchester. Workspace availability at 70% suggests a meaningful share of guests may be remote workers or business travelers, while outdoor amenities like backyards and patios (65%) reflect the market's rural Kentucky character.

Understanding Winchester's ROI Score: 51/100

Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.

How the ROI Score is Calculated

What This Means for Investors

Winchester's ROI score of 51 out of 100 places it in the 'Competitive Opportunity' band, meaning the fundamentals can work but require disciplined deal selection. The market benefits from an above-average supply/demand balance—only 20 active listings serve the area—while average revenue-to-price ratios and below-average occupancy stability and growth trends keep the score from climbing higher. Pairing this data with thorough local regulatory research and conservative occupancy assumptions will help investors identify properties where the numbers genuinely pencil out.

Short-Term Rental Regulations in Winchester

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

Permit Requirements

Short-term rental operators in Winchester, Kentucky may need to obtain a local business license or STR permit before listing their property. Investors should verify current requirements directly with the City of Winchester and Clark County authorities, as rules in smaller Kentucky municipalities can change with limited notice.

Key Restrictions

Common STR restrictions that may apply include occupancy limits, noise ordinances, parking requirements, and minimum-stay mandates. HOA covenants can also restrict or prohibit short-term rentals in certain neighborhoods, so reviewing any deed restrictions is essential before purchasing an investment property.

Tax Obligations

Kentucky imposes a state transient room tax, and Clark County or the City of Winchester may levy additional local lodging or occupancy taxes on short-term stays. Many booking platforms collect and remit some of these taxes automatically, but hosts should confirm their full obligation with a local tax professional.

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

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, Winchester's STR landscape is likely to see continued supply growth as investor attention increases, but occupancy may remain in the 24–28% range unless local demand drivers strengthen. Seasonal patterns suggest October will continue to be the standout revenue month, with winter months remaining soft. ADR could inch up modestly—perhaps 1–3%—as newer, better-appointed listings enter the market, though below-average occupancy stability and market growth trends call for conservative underwriting. Investors entering now should plan for pronounced seasonality and build reserves for the January–February lull."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winchester, KY

What is the average Airbnb occupancy rate in Winchester?

The average Airbnb occupancy rate in Winchester, KY is currently 26%, which is slightly below the Kentucky state average of 28%. Occupancy varies significantly by property size—one-bedroom listings average 38% occupancy while two-bedrooms sit at 18%. These figures reflect trailing performance and individual results can vary based on pricing strategy, listing quality, and seasonal demand.

How much do Airbnb hosts make in Winchester?

Airbnb hosts in Winchester earn an average of $1,552 per month and approximately $18,629 per year based on trailing 12-month booking data. Revenue varies by property size: one-bedroom listings average about $16,184 annually, while two-bedroom properties earn roughly $29,950 per year. Peak months like October can push monthly revenue above $2,700, while winter months may drop below $650.

Is Winchester a good market for Airbnb investment?

Winchester earns a Rabbu ROI Score of 51 out of 100, placing it in the 'Competitive Opportunity' category. The market has a favorable supply/demand balance with only 20 active listings, and average home values around $399K provide an accessible entry point. However, below-average occupancy stability and market growth trends mean investors need to be selective about deal sourcing and property positioning to generate strong returns.

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

The average daily rate for Airbnb listings in Winchester is $139, which is significantly below the Kentucky state average of $333. One-bedroom properties command an average ADR of $96, while two-bedroom listings average $169. The lower ADR relative to the state reflects Winchester's positioning as a smaller, more affordable market.

Are short-term rentals legal in Winchester?

Short-term rentals generally operate in Winchester, KY, but operators may need to secure local permits or business licenses. Regulations can vary and evolve, so prospective investors should check directly with the City of Winchester and Clark County officials for the most current requirements, including any zoning restrictions or HOA covenants that may apply.

When is peak season for Airbnb in Winchester?

Peak season in Winchester is October, when average monthly revenue reaches $2,765—nearly five times the January low of $597. The broader warm-weather season from April through November generally performs well, with most months generating between $1,674 and $1,950. Winter months (December through February) represent the slowest period, so investors should budget accordingly for seasonal cash-flow swings.

How many Airbnbs are there in Winchester?

Winchester currently has 20 active Airbnb listings as of April 2026. The supply is concentrated in smaller property sizes, with 9 one-bedroom and 6 two-bedroom listings making up the tracked inventory. Year-over-year listing growth of 188% indicates the market is attracting new hosts, though the small base means even a handful of new listings can significantly change the competitive landscape.

How is Airbnb revenue calculated in Winchester?

The annual and monthly revenue figures for Winchester 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, remove regional outliers, and roll the results up to a market-level historical average. This approach anchors the figures to what hosts have actually earned recently while 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 Winchester, KY
• Occupancy rates, average daily rates, and RevPAN trends by property size
• Monthly and annual revenue estimates based on trailing 12-month booking performance
• Home value data sourced from the Zillow Home Value Index (ZHVI)
• Amenity prevalence and supply distribution across bedroom configurations

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing performance as of the date noted and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations vary and should be independently verified before investing.