With the Island’s vacation rental market continuing to attract more homeowners, Vineyard towns are considering new bylaws to locally regulate the short-term rental industry.

On the state level, short-term rentals are subject to new requirements, including registration with the Massachusetts Department of Revenue and annual inspections for certain units. This spring, Oak Bluffs, Chilmark and Tisbury are hammering out regulations on the municipal level — an undertaking some officials say boils down to balancing the Island’s tourist economy with its pressing housing crisis.

Though Island property owners have long rented space in their homes to seasonal vacationers, the rise of Airbnb and Vrbo as convenient rental platforms has increased the presence of short-term rentals on the Island, giving rise to questions about these rentals’ impacts on the year-round community.

In the Martha’s Vineyard Commission’s 2024 housing needs assessment, the commission found that short-term rentals, while offering millions per year in Islandwide tax revenue, erode the Island’s stock of attainable year-round housing. In total, the commission found that the Island’s 4,000 short-term rentals dwarfs its supply of year-round rentals, of which there are roughly 1,600.

Oak Bluffs could limit homeowners to one short-term rental. — Ray Ewing

West Tisbury was the first Island town to create a short-term rental bylaw in 2024, when voters approved regulations that require all short-term rentals be registered with the town. The bylaw also limited owners to a single short-term rental property that the owners have to occupy for 30 days a year.

Bea Phear, a member of the West Tisbury short-term rental committee that helped develop the bylaw, said that the town had three major goals: to prevent corporations from buying up housing stock, to protect year-round residents’ ability to occasionally rent their homes and to maintain West Tisbury’s character.

Ms. Phear said the committee was divided on the bylaw’s impact on year-round housing stock.

“There were some people who believed that every short-term rental essentially displaced a permanent, year-round rental or a year-round person. I’m not in that school,” she said. “I think that a lot of real estate that could have gone to short-term rentals would have instead gone to seasonal residents and not been in the long-term rental market stock anyway.”

West Tisbury town administrator Jennifer Rand said that the town is slowly working on putting the bylaw into practice.

“The voters asked that [short-term rentals] be registered and inspected, and that’s what we’re doing, and that’s slowly happening,” she said.

At town meeting in April, Oak Bluffs voters will evaluate a new short-term rental bylaw developed by the Oak Bluffs planning board’s zoning reform subcommittee.

Similar to West Tisbury’s bylaw, the proposed Oak Bluffs bylaw would require registration of short-term rental properties with the town and would require that owners reside in their properties for at least 30 days a year. Additionally, it would prevent a single owner from operating more than one short-term rental, angling to block large companies from buying up the town’s housing stock.

Planning board vice chair Chris Chambers said that the new bylaw would help protect Oak Bluffs residents’ right to rent their properties while also safeguarding housing for year-round residents.

He cited recent short-term rental lawsuits on Nantucket that dinged the town and property owners for allowing short-term rentals in certain historic districts when town bylaws didn’t explicitly allow them. Nantucket residents voted down a local short-term rental bylaw at six separate town meetings, but in late 2025 approved short-term rentals as a legal property use.

“We’re already delinquent on this,” Mr. Chambers said at the December meeting. “All it takes is for one person to have an issue and all our short-term rentals vaporize.”

Chilmark voters will also have the chance to vote at town meeting on a bylaw officially permitting short-term rentals. Per the Martha’s Vineyard Commission, Chilmark has more than 400 short-term rentals.

The proposed bylaw, sponsored by the planning board, permits short-term rentals as an accessory use of residential properties. Unlike the West Tisbury bylaw and the bylaw before voters in Oak Bluffs, the Chilmark bylaw does not include provisions about lengths of stay or yearly caps on nights rented.

Planning board chair Richard Osnoss said the Nantucket lawsuit was a major impetus behind the proposed bylaw. He also said that having a bylaw on the books will allow the town to refine it in the future if a need for tighter regulations presents itself.

“We wanted to address that and enable people to continue renting in a legal fashion,” he said.

A former version of the bylaw, which was never voted on, included more stringent rules, including capping the number of nights a property is rented in a calendar year at 95. Mr. Osnoss said that the board removed these specific provisions because they may have harmed residents who have long relied on renting their homes as a source of income.

“It got to the point where we felt like the bureaucracy we were potentially putting in place would be more harmful than beneficial,” he said.

While Mr. Osnoss emphasized the bylaw’s potential to prevent legal trouble like Nantucket’s while giving the town future leverage over short-term rental regulation, he isn’t sure it will meaningfully impact Chilmark’s year-round housing stock.

“Would people all of the sudden rent year-round? I don’t know...” he said. “It’s a problem that I don’t know we’ll ever be able to fix.”

In Edgartown, a short-term rental committee is hoping to get permission at spring town meeting to spend $80,000 on a short-term rental study through the Donahue Institute at the University of Massachusetts Amherst. Officials hope it will provide a full picture of how many short-term rentals are in town and how they are affecting the community.

“The scope of this study would be to measure and understand aspects of the short-term rental market in Edgartown, with the purpose of providing the town and public with a fuller description of short-term rentals in the community,” said Edgartown short-term rental committee member Casey O’Connor.

Alex Morrison, a select board member and the chair of the short-term rental committee, felt the study is important for Edgartown, which he said has roughly 1,400 short-term rentals per the town’s count.

He echoed Mr. O’Connor’s sentiment that having concrete data from the study will be important for deciding how to move forward, especially if it can provide insight into the impact of short-term rentals on the housing crisis.

“We know we have a housing crisis on Martha’s Vineyard [and in] Edgartown,” he said. “[The study] would better help us understand how we can help.”

But he also noted a desire to balance that objective with the need to keep attracting summer short-term renters, whom he said are vital to Edgartown’s economy.

“We still want to make sure we have a great vacation experience for all the people that come here that we rely on,” he said. “We want to make sure that we’re making calculated decisions with their best interest in mind.”

Mr. Morrison said that enforcement of short-term rental regulations is challenging given staffing limitations at the municipal level. He noted that the state’s new inspection requirements for short-term rentals has already created a lot of work for Edgartown’s building department. Adding more rules would likely require even more manpower to enforce.

While some Island towns are trying to implement more restrictions on the short-term rental market, one town is exploring rolling a certain restriction back.

At Tisbury’s town meeting on April 28, voters will decide whether to abolish the town’s current 75-night annual limit on short-term rentals, while also raising the local tax on professionally-managed short-term rentals from 6 per cent to 9 per cent. The tax increase is made possible by a state law allowing towns to charge a community impact fee on top of the state’s short-term rental tax for properties under an owner that operates two or more rentals.

Tisbury select board chair Roy Cutrer drafted the bylaw. He said at a meeting last month that dropping the 75-night limit, passed by voters in 2024, while simultaneously raising the tax will help the town collect more revenue. He also said that the cap as currently specified could discourage rental operators from investing in properties in town.

“By limiting those nights, we’re limiting the town’s revenue,” he said.

In 2024, the Tisbury affordable housing committee sponsored a joint short-term rental study with Oak Bluffs conducted by outside consultants. Per the report, 726 short-term rental units have been registered in town since 2019, representing 138 per cent growth in that five-year period. The report also found that 14 per cent of short-term rental listings were not registered with the Department of Revenue, representing roughly $181,000 in uncollected tax revenue.

Victor Capoccia, a member of the Tisbury affordable housing committee, questioned the benefit of raising the tax when there is existing tax revenue from short-term rentals that has gone uncollected.

“I think we’re leaving money on the table,” he told the Gazette.

Mr. Capoccia also fears abolishing the 75-night cap could encourage property investors to eat into year-round housing in a community that already lacks it.

“The reality is, there’s teachers, there’s health care workers, there’s public employees, there’s nonprofit employees who are commuting and who, under normal circumstances, would be residents of the community in which they work and they serve,” he said.

But he also noted his sensitivity to the Island’s tourist economy. The balancing act between prioritizing tourism and year-round housing, he said, is a crucial one.

“This is not about squashing tourism,” he said. “This is about establishing a balance that allows residents to be able to live in an environment in which they have a community they can contribute to.... This is about both, and it’s not either or.”