Short-term rentals across Massachusetts

Beyond Boston and Cape Cod, Massachusetts has a spread of smaller short-stay markets: the North Shore around Salem, Gloucester and Rockport; the South Shore and Plymouth; Worcester and the center of the state; the Pioneer Valley around Northampton and Amherst; and the Berkshires, with Lenox, Stockbridge, Great Barrington and the summer concerts at Tanglewood. Demand comes from college visits and graduations, hospitals, business travel, autumn color, October in Salem and summer culture in the hills. The housing is just as varied: two- and three-family houses, condos, farmhouses and cottages.

One state regime everywhere

Since July 1, 2019, anyone operating a short-term rental must register each property with the Department of Revenue through MassTaxConnect and collect the state room occupancy excise of 5.7% (5% plus a 0.7% surtax), unless the unit is rented 14 days or less a year. Cities and towns may add a local excise of up to 6%, and a community impact fee of up to 3% on professionally managed units and on some owner-occupied two- and three-family houses. Worcester, Springfield, West Springfield and Chicopee also carry a convention center surcharge. Every operator needs $1 million of liability insurance per unit, unless the platform provides equal cover.

Many local regimes

The law leaves the use itself to municipalities, and they diverge. Boston, treated separately, allows only owner-occupied rentals under its 2018 ordinance. Elsewhere, requirements range from simple registration to owner-occupancy rules or caps on days per year. In the Berkshires, Great Barrington adopted its own rules in 2022 after a long debate, and neighboring towns have followed with bylaws of varying strictness. Because a town meeting can change a bylaw in one evening, the check must be recent.

Our advice

• Before buying, ask the building or zoning office whether short-term rentals are allowed in the district and whether the owner must live on site.
• Owners who live in one unit of a two- or three-family house are usually in the strongest position under local rules.
• Register with the Department of Revenue and confirm insurance before the first guest.
• Price around the academic calendar, foliage weeks and local festivals, and consider furnished stays of a month or more near hospitals and campuses.

We study every request and tell you honestly whether and how we can help.

The convention center surcharge, and what it changes

Worcester, Springfield, West Springfield and Chicopee stack a convention center financing surcharge on top of the state excise and any local option, on top of the community impact fee where it applies to a professionally managed unit. A guest booking a weekend in Worcester during a graduation or a convention can see four separate charges on the final bill, and a listing that shows only the state 5.7% will look cheaper than it turns out to be once the platform adds the rest at checkout. Getting the math right at listing time avoids disputes after the stay.

The distinction between owner-occupied and non-owner-occupied two- and three-family houses runs through both the community impact fee and, indirectly, through insurance pricing: an owner living in one unit typically pays less for liability cover than an absentee owner of the same building, because the insurer treats the arrangement as closer supervision. Confirm which category your address falls into before quoting a nightly rate that assumes the lighter fee schedule.