Boston vs Milwaukee
Massachusetts Legal but Limited | Wisconsin Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Milwaukee, Wisconsin |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $25 registration fee | $110 annual license + $300 one-time pre-inspection fee |
| Tax Rate | 6.5% state excise + 6% city convention center tax | 5% state sales + 3% county room tax + 7% city room tax (15% combined) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $300/day for unregistered listing | $150–$500 first offense; steeper fines and permit revocation for repeat offenses |
| Verdict | Milwaukee has more favorable STR regulations overall. | |
Boston, Massachusetts
Status Legal but Limited
Permit Fee $25 registration fee
Tax Rate 6.5% state excise + 6% city convention center tax
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $300/day for unregistered listing
Milwaukee, Wisconsin
Status Legal with Permit
Permit Fee $110 annual license + $300 one-time pre-inspection fee
Tax Rate 5% state sales + 3% county room tax + 7% city room tax (15% combined)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $150–$500 first offense; steeper fines and permit revocation for repeat offenses
Milwaukee has more favorable STR regulations overall.
Boston Overview
Only primary-residence units may be listed as STRs. Investor-owned (non-owner-occupied) short-term rentals are prohibited. Must register with the city and carry $1M liability insurance.
Full Boston guide →Milwaukee Overview
Tourist Rooming House license required for rentals under one month. Properties must pass safety inspection for building code and fire safety compliance before license is issued.
Full Milwaukee guide →Frequently Asked Questions
Is it easier to Airbnb in Boston or Milwaukee?
Boston is classified as "Legal but Limited" while Milwaukee is "Legal with Permit." Boston's permit fee is $25 registration fee compared to $110 annual license + $300 one-time pre-inspection fee in Milwaukee.
Which city has higher STR taxes — Boston or Milwaukee?
Boston charges 6.5% state excise + 6% city convention center tax, while Milwaukee charges 5% state sales + 3% county room tax + 7% city room tax (15% combined). Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Milwaukee: $150–$500 first offense; steeper fines and permit revocation for repeat offenses.