This month, West Tisbury is joining an initiative that aims to turn short-term rentals into year-round housing by providing a cash incentive to prospective landlords.
The program, called Lease to Locals, has been piloting in Chilmark since last August. In its year of operating in the up-Island town, Chilmark has created five new year-round rentals, housing 11 Island residents, officials said. The program also operates on Nantucket and in Provincetown.
West Tisbury voters approved the measure at April’s town meeting, allocating $150,000 to fund the program for one year. Funding will offset rental prices and pay for Placemate, which handles landlord and tenant applications, pairings and advertising.
“We all know we’re in a housing crisis,” Kim Angell, chair of the affordable housing committee in West Tisbury, told the Gazette. “The problem is not that we don’t have enough houses, it’s that we don’t have enough houses available for year-round occupants.”
West Tisbury will partner with Chilmark to try to change that.
The program provides a one-time cash incentive between $4,000 and $12,000 per year for property owners to convert homes sitting vacant or previously rented on a short-term basis into a year-round rental unit. Properties are subject to a maximum rental rate ranging from $2,900/month for a studio to $4,250/month for a three-bedroom unit.
Lease terms are for one year, with the hope that tenants and landlords renew. In Chilmark, a “significant” number of tenants have renewed their leases, according to Peter Cook, chair of the Chilmark affordable housing committee.
“It seems like a small advance, but the way it’s happening is very encouraging,” said Mr. Cook.
Chilmark previously launched the program as a 18-month pilot. The town is currently renewing it for another year, and has two more units in the pipeline for becoming year-round housing.
Chilmark is funding Lease to Locals with a seasonal communities grant, as well as a 2 per cent excise tax that goes to the housing trust. In the past year, Chilmark has raised $200,000 with the tax, using only half of that for the program, according to Alison Kisselgof, administrator of the affordable housing committee in Chilmark.
Mr. Cook and Ms. Angell agreed that the program is a short-term solution, but one with momentum as other organizations work towards creating more housing opportunities for Island residents.
“It gives people an opportunity to remain here and live to fight another year, finding more permanent housing or perhaps a project gets completed in the meantime,” said Ms. Angell.
Chilmark and West Tisbury will both pay $2,500 a month for Placemate’s services, said Ms. Angell. The towns will share meetings and marketing initiatives, lowering the administration costs for each town — Chilmark previously paid $3,500 a month for the service.
The program allows homeowners to choose their tenants, establishing relationships that has often led to lower rates, said Ms. Kisselgof.
Ms. Angell said that there has already been interest in the program among tenants and landlords in West Tisbury. She is hoping for 10 new homes to enter the year-round market in West Tisbury.
Ms. Kisselgof is excited that West Tisbury is joining the program, she said.
“West Tisbury joining us in the second year is going to be huge,” she said. “Getting it Islandwide is a goal.”
Other towns are also interested in adopting the program. Officials from Aquinnah have reached out to Ms. Angell, she said, and officials are expecting Tisbury to join the effort as well.
“If we can build on it, that’d be fantastic,” said Ms. Angell.
This article appears in August 14, 2026.
Giant percentage of our island is under 3 acres zoning. It’s lovely for conservation efforts, but it’s made it so that the down is Townes are servicing the rest of the islands. The imbalance is real. You can’t enjoy 3 acres zoning and complain there isn’t enough housing.
This is a good idea. I just wish it wasn’t funded by taxpayers. Vineyard Haven taxpayers are already burdened with horribly high tax bills. Can we add a surcharge for the ferry or up the tax on short term rentals to pay for this?
This is a start. I didn’t see Tisbury or Oak Bluffs mentioned in this article. Tisbury only has to remove some of its restrictions on deeds in their bylaws and people could rent the house and guest house to year rounders and not be punished $300.00 a day.
WAKE UP!
I’m curious how someone can get in on this deal who has already been doing the right thing by renting year round to a local tenant for an affordable rate. I’d be happy to collect additional rent so long as my year round tenant doesn’t have to pay it.