Winchester

As of May 2026, Winchester, Front Royal, Harpers Ferry have 386 active Airbnb and VRBO listings. This represents a 4% decrease from the previous year.

The average Airbnb or VRBO in Winchester generates $35K per year. High-performing properties earn $80K/year, while low-performing properties earn $17K/year. The substantial revenue spread suggests that market performance is highly bifurcated, with top earners capturing significantly more value despite the overall 25% year-over-year revenue decline.

Average home prices in Winchester vary by property size: 1-bedroom properties cost approximately $190K, 2-bedroom homes average $279K, 3-bedroom properties are around $327K, and 4+ bedroom homes average $527K. These prices reflect median home values across the Winchester, Front Royal, Harpers Ferry area.

Airbnb and VRBO can be profitable in Winchester, with an average gross yield of 10% across all properties. High-performing properties achieve yields up to 22%, which is considered top for short-term rental investment. This wide yield variance indicates that profitability is heavily dependent on specific asset-level performance rather than broad market trends.

The average occupancy rate for Airbnbs and VRBOs in Winchester is 35%. This occupancy level, combined with an average nightly rate of $244, results in a RevPAR (revenue per available room) of $69 per day.

2-bedroom properties demonstrate the strongest performance in Winchester, with an average gross yield of 13% and annual revenue of $35K. These properties balance purchase price ($279K), operating costs, and rental demand most effectively in the Winchester market.

Short-term rental regulations vary by jurisdiction in the Winchester area. Winchester, VA: Moderate. Zoning permit required, must comply with residential district rules. Some enforcement through complaints. Front Royal, VA: Lenient. No specific STR regulations, general business license may apply. Minimal enforcement. Harpers Ferry, WV: Lenient. No municipal STR regulations, state lodging tax collection required. Light enforcement, primarily tax-focused. Always verify current regulations with local authorities and obtain necessary permits before operating a short-term rental.

The Winchester Airbnb and VRBO market is currently showing balanced conditions. Supply has declined 4% year-over-year, while RevPAR has decreased 26%. This indicates balanced supply-demand dynamics. The drop in RevPAR despite lower supply suggests a softening in traveler demand or spending power that outweighs the contraction in available inventory.

Launch around August, 2-3 months before peak fall season (November peaks). This pre-peak timing lets you build reviews when competition is -28% lower than peak months. Avoid launching during peak season when established listings dominate, or slow months (March-January) when gaining traction is harder.

The most common amenities in Winchester listings include: Air Conditioning (96%), Kitchen (95%), Tv (87%), Heating (72%), Washing Machine (69%). Amenities that boost revenue the most include Air Conditioning, Hot Tub, Washing Machine, with Air Conditioning properties earning approximately 103% more ($46K/year vs $23K/year).

Monthly estimated revenue per listing in Winchester over the last 12 months: May: $2K, June: $2K, July: $2K, August: $3K, September: $2K, October: $2K, November: $2K, December: $2K, January: $2K, February: $1K, March: $2K, April: $2K. These figures are based on RevPAR (revenue per available room) multiplied by the number of days in each month.

The overall average nightly rate in Winchester is $244, up 9% year-over-year. By property size: 1-bedroom properties average $171/night, 2-bedroom properties average $201/night, 3-bedroom properties average $251/night, 4+ bedroom properties average $473/night. Rates peak in December and are lowest in March.

Guests in Winchester book an average of 33 days in advance, down 16% from last year. By property size: 1-bedroom: 29 days, 2-bedroom: 30 days, 3-bedroom: 35 days, 4+ bedroom: 43 days. Larger properties tend to have longer booking windows as guests plan group trips further ahead.

Over the past year, the Winchester Airbnb and VRBO market has seen the following changes: supply declined 4%, revenue per listing decreased 26%, occupancy fell 15%, average nightly rates increased 9%, and lead time decreased 16%. These metrics reflect a market struggling with lower utilization, where higher rates are failing to compensate for reduced occupancy.

In Winchester, Saturday sees the highest booking demand while Tuesday has the lowest. Nightly rates peak on Friday and are lowest on Tuesday. Weekends show 80% higher occupancy than weekdays.