Short-term rentals
Boston allows stays under 28 days only in owner-occupied condos and one-, two- and three-family buildings, and the owner must live there at least nine months of every twelve.
For investors: A non-owner-occupied Boston two-family bought purely as an investment cannot host stays under 28 days at all. Inspectional Services asks for two proofs of residence, such as a residential exemption record or a voter certificate, so plan for furnished leases of 28 days or more instead.
Source: City of Boston Inspectional Services, Short-Term Rentals, Oct 2026
An owner-occupant of a Boston two- or three-family can register their own home plus one owner-adjacent unit; yearly fees are $25 for a room with the owner present and $200 for a whole unit.
For investors: Only one whole unit may be offered at a time, so the owner-adjacent unit and the owner's own home cannot both run as whole-unit rentals while the owner is away. Boston registrations renew every year and do not transfer when the building sells.
Source: City of Boston Inspectional Services, Short-Term Rentals (fees repeated in the city's 2025 Short-Term Rentals Report to the City Council), Oct 2026
Boston's short-term rental ordinance fines $300 a day for listing an ineligible unit and $100 a day for an unregistered eligible one, and operators must notify abutters within 300 feet within 30 days of registration.
For investors: Each day of noncompliance counts as a separate violation, and a booking agent that takes a fee for an ineligible Boston unit faces the same $300 daily fine, so a listing that fails the owner-occupancy test carries real cost for host and platform alike.
Source: City of Boston, Short-Term Rental Ordinance (Code sections 9-14.5 and 9-14.9), linked as the current ordinance from the ISD short-term rental page, Oct 2026
The state's local tax databank lists Boston's room occupancy excise at 6.5% since July 1, 2019, plus a 3% short-term rental community impact fee that reaches owner-occupied two- and three-family units.
For investors: Boston opted to apply the impact fee inside owner-occupied two- and three-family houses, which is exactly where its owner-adjacent units sit. Budget both city charges on top of the state excise when comparing nightly income with a standard twelve-month lease.
Source: Massachusetts DOR Division of Local Services, Room Tax and Impact Fee report (data current as of 2026-10-12), Oct 2026