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

Winchester Short-Term Rental Market Overview

Winchester, VA is a small but growing short-term rental market with 59 active Airbnb listings and an average annual revenue of $23,253 per property. While the average daily rate of $146 sits well below the Virginia state average of $339, occupancy at 35% slightly edges out the statewide figure, suggesting steady — if modest — demand. The market's 176% year-over-year growth in active listings signals rising investor interest, though competition is tightening and deal sourcing will need to be strategic.

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 Mar, 17 2026.

Why Investors Consider Winchester

Winchester attracts STR investors with its above-average occupancy stability and proximity to the Shenandoah Valley's tourism corridor, though tighter competition and higher property prices require careful deal selection.

Expert Market Assessment

"Winchester presents a competitive opportunity for STR investors who are willing to be selective. Revenue potential is real — 3-bedroom properties can generate around $30,624 annually — but with average home values at $581,245, the revenue-to-price ratio falls below average, meaning not every property will pencil out. Seasonality is noticeable: July peaks at $2,717 in average monthly revenue while February dips to $1,310, creating roughly a 2:1 spread between the strongest and weakest months. Investors who target well-located 2- or 3-bedroom properties and price dynamically through shoulder seasons stand the best chance of outperforming the market average."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winchester

Average revenue by month in Winchester

Winchester's revenue pattern shows clear seasonality, peaking in July at $2,717 and bottoming out in February at $1,310 — a spread of over $1,400. A secondary autumn bump in October ($2,217) suggests fall tourism plays a meaningful role, giving investors two distinct earning windows to optimize around.

Active Airbnb listings by property size in Winchester

One-bedroom units dominate the supply with 27 listings (46% of the market), followed by 16 two-bedroom and just 10 three-bedroom properties. The relatively thin supply of 3-bedroom listings could represent an opportunity for investors, particularly since those units generate the highest monthly revenue.

Average daily rate (ADR) by property size in Winchester

ADR rises predictably with property size, from $112 for 1-bedroom units to $192 for 3-bedrooms — a 71% premium. The jump from 1-bedroom to 2-bedroom ($112 to $148) delivers a strong rate increase without the higher acquisition cost of larger homes, making 2-bedrooms an appealing middle ground.

Average RevPAN by property size in Winchester

Two-bedroom properties lead in RevPAN at $59, narrowly edging out 3-bedrooms at $58, while 1-bedroom units trail at $38. This indicates that 2-bedroom listings deliver the best revenue efficiency after accounting for occupancy, making them the sweet spot for income per available night.

Average occupancy rates by property size in Winchester

Two-bedroom listings boast the highest occupancy at 40%, a full 10 percentage points above 3-bedroom units at 30%, with 1-bedrooms splitting the difference at 34%. For cash-flow-conscious investors, the 2-bedroom segment offers the most predictable booking frequency in Winchester.

Average monthly revenue by property size in Winchester

Monthly revenue climbs with property size, from $1,501 for 1-bedrooms to $2,552 for 3-bedroom listings, though the gap between 2-bedrooms ($2,008) and 3-bedrooms is relatively modest at $544. This suggests diminishing marginal returns as you scale up, especially when factoring in higher acquisition and operating costs for larger properties.

Average annual revenue by property size in Winchester

Three-bedroom properties deliver the highest annual revenue at $30,624, outpacing 2-bedrooms ($24,100) by about 27% and 1-bedrooms ($18,023) by 70%. However, given that 2-bedroom units achieve nearly identical RevPAN with higher occupancy, they may offer a more reliable return relative to purchase price for many investors.

Most common amenities for Airbnb listings in Winchester

Parking (92%) and a full kitchen (90%) are near-universal expectations among Winchester's Airbnb guests, while self check-in (78%) and laundry facilities (76%) round out the top tier. Outdoor amenities like backyards (58%) and patios (53%) are common differentiators, and the relatively low prevalence of hot tubs (10%) signals a potential way to stand out in this market.

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 market has genuine demand but requires disciplined deal sourcing to achieve attractive returns. Occupancy stability scores above average, which is encouraging for cash-flow consistency, but the below-average revenue-to-price ratio — driven by home values near $581,245 against $23,253 in average annual revenue — means investors need to find properties priced below the market median or capable of outperforming on rates. We recommend pairing this data with thorough local regulatory research and a clear understanding of Winchester's zoning and permitting landscape before committing capital.

Short-Term Rental Regulations in Winchester

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

Permit Requirements

The City of Winchester and the state of Virginia may require short-term rental operators to obtain a business license or STR permit before listing a property. Investors should verify current registration requirements directly with the Winchester city government and the Virginia Department of Taxation before purchasing.

Key Restrictions

Common restrictions in Virginia STR markets include occupancy limits, minimum stay requirements, noise ordinances, and parking provisions. HOA rules can also impose additional limitations — especially in planned communities — so investors should review any applicable covenants. Some municipalities in Virginia have also explored permit caps, making it important to check Winchester's most current local ordinances.

Tax Obligations

Short-term rental hosts in Virginia are typically subject to state and local transient occupancy taxes, as well as applicable sales tax. Major platforms like Airbnb often collect and remit some of these taxes on behalf of hosts, but operators should confirm their full obligations with the Virginia Department of Taxation to ensure compliance.

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 market is expected to see continued supply growth as investor awareness increases, which could put mild downward pressure on occupancy unless demand keeps pace. Seasonal patterns suggest revenue will concentrate in the summer months — particularly July and August — with softer winter performance, so investors should plan cash reserves accordingly. ADR may see modest increases in the range of 1–3% as hosts refine pricing strategies, and occupancy is likely to settle around 33–37% market-wide. Investors entering now should focus on 2-bedroom configurations, which currently offer the strongest balance of occupancy and revenue efficiency."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winchester, VA

What is the average Airbnb occupancy rate in Winchester?

The average occupancy rate for Airbnb listings in Winchester is currently 35%, which is slightly above the Virginia state average of 34%. Occupancy varies by property size, with 2-bedroom units leading at 40% and 3-bedroom properties trailing at 30%. This suggests that mid-sized properties tend to attract the most consistent bookings in this market.

How much do Airbnb hosts make in Winchester?

On average, Airbnb hosts in Winchester earn approximately $1,937 per month or $23,253 per year based on trailing 12-month booking data. Revenue varies significantly by property size: 1-bedroom listings average $18,023 annually, 2-bedrooms bring in around $24,100, and 3-bedroom properties lead at $30,624. Individual results depend on factors like location, pricing strategy, and property quality.

Is Winchester a good market for Airbnb investment?

Winchester carries an ROI score of 51 out of 100, placing it in the "Competitive Opportunity" category. The market benefits from above-average occupancy stability, but the revenue-to-price ratio is below average given home values near $581,245. Investors who source deals carefully and target the right property size — particularly 2-bedroom units with strong RevPAN — can find viable opportunities, but this isn't a market where every listing will deliver strong returns.

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

The average daily rate across Winchester's Airbnb market is $146, well below the Virginia state average of $339. ADR scales with property size: 1-bedroom listings average $112 per night, 2-bedrooms come in at $148, and 3-bedroom properties command $192. The lower rates compared to the state reflect Winchester's more affordable positioning relative to Virginia's coastal and metro-adjacent markets.

Are short-term rentals legal in Winchester?

Short-term rentals are generally permitted in Winchester, VA, though operators may need to obtain applicable permits or business licenses. Regulations can vary and may include requirements around zoning, occupancy limits, and tax registration. We strongly recommend checking directly with the City of Winchester and the Virginia Department of Taxation for the most current rules before investing.

When is peak season for Airbnb in Winchester?

Peak season for Airbnb in Winchester runs from June through August, with July standing out as the top-earning month at an average of $2,717 in revenue. October also performs well at $2,217, likely driven by fall foliage tourism in the Shenandoah Valley. The slowest months are January and February, when average revenue dips to around $1,310–$1,375.

How many Airbnbs are there in Winchester?

As of April 2026, there are 59 active Airbnb listings in Winchester. The market has seen significant growth, with a 176% year-over-year increase in active listings. The supply is heavily weighted toward smaller units, with 27 one-bedroom listings making up nearly half of all inventory, followed by 16 two-bedroom and 10 three-bedroom properties.

How is Airbnb revenue calculated in Winchester?

The annual and monthly revenue figures shown for Winchester are derived from the trailing 12 months of historical booking performance for active comparable Airbnb listings in the market — they are not forward-looking projections. We average each comparable listing's actual revenue per available night (RevPAN) by month over the past year, remove regional outliers, and roll the remaining data up to a market-level historical average. This approach anchors figures to what hosts have actually earned recently, while naturally reflecting seasonal peaks (like July at $2,717) and slower months (like February at $1,310) 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 and surrounding zip codes
• Average daily rates, occupancy rates, and RevPAN tracked over time by property size
• Monthly and annual revenue estimates based on trailing 12 months of historical booking data
• Home value benchmarks sourced from the Zillow Home Value Index (ZHVI)
• Data aggregated from multiple providers and Rabbu proprietary analytics for consistency

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 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 restrictions, and tax obligations vary — investors should verify all requirements with local authorities before purchasing.