Boston vs Portland
Massachusetts Legal but Limited | Oregon Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Portland, Oregon |
|---|---|---|
| Legality Status | Legal but Limited | Legal but Limited |
| Permit Fee | $25 registration fee | $65 (Type A single dwelling); $105 (Type A multi-dwelling) |
| Tax Rate | 6.5% state excise + 6% city convention center tax | 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Every 2 years |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $300/day for unregistered listing | Up to $26,201 across five violation types; permit revocation with 2-year ban |
| Verdict | Both cities have comparable STR regulatory environments. | |
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
Portland, Oregon
Status Legal but Limited
Permit Fee $65 (Type A single dwelling); $105 (Type A multi-dwelling)
Tax Rate 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state
Day Limit No limit
Renewal Every 2 years
Platform Tax Yes
Max Fine Up to $26,201 across five violation types; permit revocation with 2-year ban
Both cities have comparable STR regulatory environments.
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 →Portland Overview
Only accessory (hosted) short-term rentals allowed; resident must occupy the dwelling at least 270 days/year. Type A permits allow up to 2 bedrooms and 5 guests. Whole-home unhosted rentals are prohibited.
Full Portland guide →Frequently Asked Questions
Is it easier to Airbnb in Boston or Portland?
Boston is classified as "Legal but Limited" while Portland is "Legal but Limited." Boston's permit fee is $25 registration fee compared to $65 (Type A single dwelling); $105 (Type A multi-dwelling) in Portland.
Which city has higher STR taxes — Boston or Portland?
Boston charges 6.5% state excise + 6% city convention center tax, while Portland charges 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Portland: Up to $26,201 across five violation types; permit revocation with 2-year ban.