Winchester, VA
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Overview
Annual Rev
$41.8k
12 mo avg
↓1%
from prior 12 mo
Occupancy rate
40%
12 mo avg
↓4%
from prior 12 mo
Avg daily rate
$236
12 mo avg
↑10%
from prior 12 mo
Lead time
37 days
12 mo avg
↓1 days
from prior 12 mo
Revpar
$81
12 mo avg
↓11%
from prior 12 mo
Methodology note: Figures reflect Winchester market data as of September 2026. Data covers Airbnb, VRBO, and Booking.com listings. Values are seasonally influenced; rounding applied for readability.
Revenue per listing by bedroom
Bedroom count:
0
1
2
3
4+
Short-term rental supply growth
Performance metrics by bedroom
Bedrooms
Annual Rev
Avg. Zestimate
Gross yield
Supply
Amenity revenue impact
| Amenity | Est. revenue impact |
|---|---|
| Hot Tub | +30% $12,528/yr |
| Barbecue | 🔒 +1•% · $••••/yr Revenue lift and listing count available in Markets |
| Sauna | 🔒 +8% · $••••/yr Revenue lift and listing count available in Markets |
| EV Charger | 🔒 +7% · $••••/yr Revenue lift and listing count available in Markets |
| Lake Access | 🔒 +7% · $••••/yr Revenue lift and listing count available in Markets |
| Gym | 🔒 +3% · $••••/yr Revenue lift and listing count available in Markets |
| TV | 🔒 +2% · $•••/yr Revenue lift and listing count available in Markets |
| Pool | 🔒 +1% · $•••/yr Revenue lift and listing count available in Markets |
Nightly rate by day of week
Occupancy rate by day of week
Listings by channel
Listings by rental type
Listings by amenities
Listings by size
4+ bedrooms (0%)
Listings by availability
Length of stay by bedroom
1 bedroom (5.9 nights)
2 bedrooms (4.5 nights)
3 bedrooms (3.9 nights)
4+ bedrooms (3.6 nights)
Cleaning fee by bedroom
4+ bedrooms ($154)
3 bedrooms ($121)
2 bedrooms ($86)
1 bedroom ($63)
Professional host share
Professionally managed (57%)
Independent hosts (43%)
Housing market signals
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Over the 12 months ending August 2026, the Winchester market averaged 401 active Airbnb and VRBO listings, up 2% from a year earlier and up 34% over two years.
An average Winchester listing earns $37K/year. High-performing listings earn $85K, while low-performing listings earn $17K.
Median Winchester home prices by size are 1-bedroom $195K, 2-bedroom $279K, 3-bedroom $334K, and 4+ bedroom $526K.
Average gross yield is 10%, reaching 23% for high-performing listings. Gross yield excludes financing and operating costs, so net profitability varies by property.
Average occupancy in Winchester is 34%, producing RevPAR of $75 per available night.
2-bedroom listings have the highest average gross yield at 13%. They average $37K/year in revenue against a $279K median purchase price.
Rules vary across Winchester. Winchester, VA: Moderate. Zoning permit required, conditional use permit in residential zones, safety inspections. Enforcement occurs through complaint-driven process. Front Royal, VA: Lenient. Business license required, zoning compliance needed. Minimal active enforcement, mostly complaint-based. Harpers Ferry, WV: Lenient. Business registration and transient occupancy tax required. Light enforcement, primarily tax-focused rather than operational restrictions. Verify requirements for the property's jurisdiction.
The Winchester Airbnb and VRBO market appears broadly balanced. Supply has grown 2% year-over-year, while RevPAR has decreased 7%, showing no clear supply-demand imbalance.
RevPAR is highest in July and June; it is lowest in January and February.
The most common amenities are Air Conditioning (96%), Kitchen (96%), Parking (96%). The strongest positive revenue associations are Air Conditioning (+120%), Bbq (+63%), Internet (+62%).
Average daily rate in Winchester is $255, up 11% year-over-year. Rates peak in December and are lowest in March.
Guests in Winchester book an average of 34 days in advance, down 4% from last year. Booking windows range from 30 days for 1-bedroom listings to 45 days for 4+ bedroom listings.
Booking demand is highest on Saturday and lowest on Tuesday. Nightly rates peak on Friday and are lowest on Tuesday. Weekend occupancy is 82% higher than weekday occupancy.