The market runs from Cape Cod and the Islands, Nantucket and Martha’s Vineyard, through the Berkshires to Boston. Coastal property values are high, the housing stock is old, and the Cape’s season is short and crowded. Boston is effectively an owner-occupied market; the Cape and Berkshires carry the investment volume.
Nor’easters, surge, and old housesThe dominant perils are coastal: nor’easter wind, storm surge, and the flood exposure that comes with an oceanfront or harbor-side property, none of which a standard policy treats the same way. The age of the housing stock compounds it, older wiring, plaster, and roofs raise both the loss frequency and the cost to rebuild to current code.
Massachusetts claims most often fail on the coastal line: wind-versus-flood disputes after a nor’easter, where the policy covers one and excludes the other, and code-upgrade costs on older homes that ordinary policies do not fully fund. Confirm your flood coverage, your named-storm deductible, and whether you carry ordinance-or-law coverage for code upgrades.
Massachusetts runs a genuine statewide framework. The 2018 Act Regulating and Insuring Short-Term Rentals requires every operator to register with the state’s Short-Term Rental Registry and carry at least $1 million in liability coverage unless the platform provides equal or greater, and that holds even for hosts who rent few enough nights to be tax-exempt. Room-occupancy taxes reach the mid-teens once local and Cape-and-Islands water-fund surcharges apply. Boston then ties its license to owner-occupancy with daily fines, while Cape towns lean lighter on permitting but add community impact fees. Register, insure to the state minimum, and confirm the local rule before you buy.