Boston vs Portland

Massachusetts Legal but Limited | Oregon Legal but Limited

Disclaimer: General information only — not legal advice. Verify with your local government.

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.

Permits & Licensing

Boston charges $25 registration fee for STR licensing, while Portland charges $65 (Type A single dwelling); $105 (Type A multi-dwelling). Boston renewal is annual, and Portland renewal is every 2 years. Both cities share a similar regulatory stance, classified as "Legal but Limited."

Tax Obligations

In Boston, hosts pay 6.5% state excise + 6% city convention center tax. In Portland, hosts pay 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

Neither city imposes an annual day limit on short-term rentals, giving hosts year-round flexibility.

Fines & Enforcement

Hosts operating without a permit in Boston face penalties including $300/day for unregistered listing. In Portland, violations can result in Up to $26,201 across five violation types; permit revocation with 2-year ban. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

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.

Contact: Boston Inspectional Services — (617) 635-5300

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.

Contact: Portland Permitting & Development — (503) 823-2633

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. Both cities have comparable regulatory frameworks.
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.
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Boston and Portland have day limits for Airbnb?
Boston has no annual day limit. Portland has no annual day limit.
Which city is better for first-time Airbnb hosts — Boston or Portland?
For new hosts, consider the total cost of entry: Boston charges $25 registration fee for permits with 6.5% state excise + 6% city convention center tax in taxes. Portland charges $65 (Type A single dwelling); $105 (Type A multi-dwelling) with 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. Automatic tax collection in Boston and Portland makes compliance easier for beginners.