Performance indicators for the Vineyard Haven short-term rental market based on reliable data.
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The highest-performing listings in Vineyard Haven.
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Challenging to Investors
STRs are allowed but sharply constrained by a 75-night annual cap, mandatory inspections under the state building code, and dual registration (state and town) with fees (~$115 registration + $75 per inspection). Enforcement is active/rolling out, and year-round housing pressure signals further tightening, raising investor risk and limiting scalability.
Local STR Agent
STR specialist · Vineyard Haven, MA
Vineyard Haven is a community within the town of Tisbury, Massachusetts on the island of Martha's Vineyard. It is listed as a census-designated place (CDP) by the U.S. Census Bureau with a population of 2,114 as of the 2010 census.The area was called "Nobnocket" by the Wampanoag people and was first referred to by the colonial settlers as "Homes Hole", "Homes" from a Wampanoag term for "old man" and "Hole" meaning a sheltered inlet. By the 19th century, it was more commonly spelled "Holmes Hole" after the descendants of John Holmes (1730–1812) who had settled in the village during the second half of the 18th century. The village officially changed its name to Vineyard Haven in 1871. The name Vineyard Haven technically refers only to one section of the town of Tisbury, but the names are used interchangeably and Vineyard Haven is commonly used as a title for the whole town. Vineyard Haven is the main port of entry to Martha's Vineyard and one of the three main population centers (with Edgartown and Oak Bluffs). The Steamship Authority wharf is located in Vineyard Haven where ferries arrive and depart year-round. (A second, seasonal wharf is located in neighboring Oak Bluffs.) The year-round population is only about 2,000 people, but that number increases tremendously in the summer.