Lenox

Boston enforces some of the strictest short-term rental laws in the US, mandating that all units must be the host's primary residence. Investor-owned secondary units are strictly prohibited, and all hosts must register annually with the Inspectional Services Department.

Edgartown does not currently have a local municipal STR permit system, as recent attempts to pass a licensing bylaw have failed. However, hosts must comply with the Massachusetts State Registry (MassTaxConnect) and pay a combined total tax rate of 14.45%.

The Town of Stockbridge requires all short-term rentals to register annually and pass a safety inspection by the building department. The town allows both owner-occupied and secondary residences to operate as STRs, provided they meet the occupancy limits of two persons per bedroom plus two additional guests.

Amherst requires all short-term rentals to obtain a Residential Rental Permit, comply with strict occupancy limits, and prohibits STRs in accessory dwelling units (ADUs).