LicensedRental

Virginia city rules

Winchester, VA vacation rental rules and taxes

Winchester requires a zoning use permit before you start a short-term rental, which must be a single-family home or townhouse with no more than five bedrooms and ten guests. You’ll file a property management plan and allow a yearly city check. Stays pay 5.3% sales tax plus the city’s 8% lodging tax.

Checked against official sources November 7, 2026
Market
About 100 Airbnb listings
Winchester 100 (AirROI).Source
City permit
Zoning use permit
Before the first guest; it can’t be transferred to a new owner.Source
Which homes
Single-family homes and townhouses
Not apartments or mixed-use buildings, and not homes with more than five bedrooms.Source
Guests
2 adults per bedroom, 10 total
Including children. One booking at a time.Source
Taxes
5.3% sales + 8% lodging tax

Renting rooms in the home you live in (up to two rooms and four guests, with you there) is a “homeshare,” run as a home occupation.

We read Winchester’s ordinance through a third-party copy (Zoneomics). Ask the city for the permit fee and application.

Winchester is an independent city, not part of Frederick County.

What to do

  1. Check your district

    Each zoning district lists short-term rentals differently. In the RB-1 district they’re allowed by right only in the operator’s primary residence. Ask city zoning what applies at your address before you apply.Source

  2. Apply for a zoning use permit

    The owner signs the application. Include a property management plan that explains how you’ll handle complaints, trash, and noise, and name a responsible party who can respond right away. A tenant can host only with the owner’s written permission. Renting without a permit can bring a fine of up to $500 per violation.Source

  3. Register with the Commissioner of the Revenue

    Register for the city’s taxes before you rent, and keep a ledger of every stay’s dates and charges. You give it to the Commissioner of the Revenue and the Zoning Administrator once a year.Source

  4. Taxes on each stay

    Stays under 90 days owe 5.3% sales tax, and stays under 30 days also owe the local transient occupancy tax. Airbnb collects both on its bookings. If guests pay you directly, file sales tax with Virginia Tax. Winchester’s lodging tax is 8%. For direct bookings, file it with the Commissioner of the Revenue.Source

Inspection checklist

What the inspector looks for, from City of Winchester, Virginia’s published checklist.

  • Fire extinguisher in every kitchen and cooking areaIn plain view.Source
  • Smoke detectors where the building code requires
  • Carbon monoxide detector on every floor
  • Emergency information posted insideWith the manager’s contact information.Source
  • Yearly city visitApplying lets the city enter once a year, with written notice, to check the rules are followed.Source

House rules for guests

Events
Not allowed
No weddings, receptions, or other events.Source
Meals
You can’t cook for guests
Guests can use the kitchen.Source
Parking
Off street
Per the city’s parking rules; downtown parking districts have exceptions.Source
Signs
None
Source

Sources

A plain-language summary to help you prepare, not legal advice. Rules and fees change; confirm with the office before you apply. Spot something out of date? Email hello@licensedrental.com.