Thinking about “Airbnb-ing” your Williamsburg place? Quick reality check: inside city limits, STRs are true homestays, not mini-hotels; you must live there, in a single-family home, while hosting.
You can rent one bedroom, for up to 104 nights a year, and no guest can stay over 30 days. No exterior signage, keep a guest log for two years, and you’ll need a business license and to collect lodging taxes.
Tight? Yes. But with the right setup and smart management, it can still pencil out. This guide shows you how to run the numbers, stay compliant, and choose between short-term sprints or long-term steady for your bottom line and your sanity.
Short-Term Leasing: Upside and Guardrails
Imagine your Williamsburg short-term rental (STR) as booked a little over half the year, about 54% occupancy (≈197 nights), at roughly $188/night, or around $33k gross before costs; that’s a starting estimate, not a promise.
Your results depend on where the home is and what it offers, parking, pet-friendly rules, décor. How you host matters too: strong reviews, quick replies, great photos, and smart pricing usually boost bookings.
Expect income to ebb and flow, summers and holidays are brisk, while spring and late fall are quieter. Budget for per-stay cleanings, linens and minor repairs, booking-platform fees, higher utilities and internet, STR insurance, a city business license, and the cost of your time or a manager’s fee.
As of Sept 2025, add Williamsburg’s 5% lodging tax plus $2 per room-night (on top of state sales tax) to your pricing so you aren’t eating it.
And while Virginia’s 2024 law blocks brand-new special-permit hurdles for owner-occupied STRs, Williamsburg’s existing homestay rules still apply. Bottom line: STRs can beat long-term rent, if you run them like a business.
Long-Term Leasing: Stability and Simplicity
A 12-month lease is the steady-paycheck option: rent arrives on a regular schedule, cash flow is predictable, and the workload is lighter, with fewer turnovers (usually once a year), less deep cleaning, and steadier utility use that’s easier to budget.
Instead of juggling short-term permits and nightcaps, you follow Virginia’s standard landlord-tenant rules for leases, deposits, notices, repairs, and, if needed, evictions.
The trade-off is upside: you won’t capture summer price spikes, and mid-lease rent increases usually wait until renewal. If you value consistency and lower hands-on effort, a year-long lease fits.
2025 Verdict: Optimize, Don’t Gamble
Inside Williamsburg city limits, STRs are a narrow homestay lane, great upside if you qualify and run them like a hospitality business; otherwise, the year-long lease still wins for predictable income and lower effort.
Many owners do best with a hybrid: short stays in peak seasons, extended stays or a traditional lease off-peak, always aligned with city rules, taxes, and the right jurisdiction.
Confirm your property’s exact jurisdiction, run the numbers, and choose the path that fits your time and risk. If you want steady, lower-touch income…go long-term and that’s where we come in!
Ready to turn analysis into reliable rent checks? Here at One Door Realty, we specialize in long-term leasing. We handle rent-ready prep, compliant leases, fair-housing-safe marketing, thorough tenant screening, rent collection, maintenance coordination, inspections, and renewals.
Skip weekend turnovers and surprise vacancies. Keep a predictable cash flow and your free time. Hand us the keys, keep the profits, and your weekends. Let’s make your place easy to own and hard to leave empty!
FAQ
Can I switch from a long-term lease to short-term without legal risk?
Yes, if you meet Williamsburg’s homestay rules (owner-occupied, one bedroom, ≤104 nights, guest register), secure a business license and tax accounts, and confirm the correct city/county jurisdiction first.
How much more can short-term earn vs. long-term?
Potentially more in peak months (about 54% occupancy at ~$188 ADR ≈ ~$33k gross), but net profit depends on seasonality, fees, utilities, cleaning, and management.
Are regulatory changes coming that could affect STR profitability?
Yes, Virginia’s 2024 law limits new special-permit hurdles for owner-occupied STRs, but Williamsburg’s existing rules and possible 2026 lodging-tax changes still apply, so monitor both.
Additional Resources
How to Get Your House Ready to Rent in Williamsburg, VA
Decrease Vacancy With Creative Leasing Strategies in Williamsburg, VA
