Dukes County, MA Short-Term Rentals: Permit Requirements (2026)

Dukes County's STR landscape has two layers, not three: (1) state operator registration and excise, and (2) town-level rental certificates and zoning. Unlike Barnstable County (Cape Cod), Dukes County is NOT a member of the Cape Cod and Islands Water Protection Fund, so the regional 2.75% excise does NOT apply. The County government does not run a county-wide STR registry; instead, hosts must register with the Massachusetts DOR and comply with the rental ordinance of the specific Vineyard town where the property is located.

(1) STATE-LEVEL OPERATOR REGISTRATION (mandatory countywide). Under Chapter 337 of the Acts of 2018, effective July 1, 2019, the Massachusetts room occupancy excise (MGL c.64G) was extended to short-term rentals, defined as occupied stays of 31 consecutive days or less. Every operator must register with the DOR before listing or accepting bookings, regardless of how many days the property is rented per year. Registration is completed online through MassTaxConnect (mass.gov/masstaxconnect). The registration produces a Certificate of Registration as required by MGL c.62C s.67, and the operator's name and listing address are published in a public registry. Operators must collect and remit the 5.7% state room occupancy excise (5% statutory rate plus a 0.7% uncodified surtax) on every taxable booking. Hosting platforms (Airbnb, Vrbo, Booking.com) are 'intermediaries' and remit the tax on the operator's behalf for marketplace bookings; the operator remains liable for direct bookings. Returns are filed monthly through MassTaxConnect.

INSURANCE REQUIREMENT (statewide). Under MGL c.64G s.14(a), every operator must maintain liability insurance of not less than $1,000,000 per occurrence to cover the operator and any tenants or owners of the building for bodily injury and property damage arising from the rental. If the hosting platform provides equal or greater coverage, the platform's coverage satisfies the requirement.

14-DAY EXEMPTION (LIMITED). Massachusetts removed the prior broad 14-day exemption for the room occupancy excise effective July 1, 2019. Operators who rent 14 days or fewer per calendar year are exempt from collecting the excise but are still required to register with DOR and provide insurance.

CAPE COD AND ISLANDS WATER PROTECTION FUND (DOES NOT APPLY ON MARTHA'S VINEYARD). Under MGL c.64G s.3C and 830 CMR 64G.1.1, the 2.75% Cape Cod and Islands Water Protection Fund excise applies only in member towns. As of the latest data, no Dukes County town (and no Nantucket town) has voted at town meeting to join the Fund. All six Vineyard towns are pursuing comprehensive wastewater management plans that would be a precondition to joining, but until and unless they opt in by majority vote of town meeting, the 2.75% does NOT apply to Vineyard STR bookings. The combined Vineyard STR tax therefore is 11.7% (5.7% state + 6% local), not 14.45%.

(2) TOWN-LEVEL RENTAL CERTIFICATE / PERMIT (varies by town). Under MGL c.64G s.3A and the Home Rule Amendment, each Vineyard town may adopt a local option room occupancy excise of up to 6% and may regulate STR operators by local bylaw. All six Vineyard towns have adopted the 6% local excise. Town STR rules differ:

- TISBURY (Vineyard Haven): Annual rental certificate of registration required for each rental unit under the Tisbury Building & Zoning Department. Reported certificate fee: $115/year per unit; biannual inspection fee: $75. Apply through the Tisbury online permitting portal under Building and Zoning > Short Term Rental. Phone: 508-696-4280. Tisbury also imposes a 75-night annual cap on short-term rentals; voters reaffirmed the 75-night cap at the April 28, 2026 town meeting after the Select Board's proposal to remove it failed to reach a two-thirds majority.

- WEST TISBURY: Short-term rental bylaw adopted at April 2024 town meeting; received Attorney General approval July 7, 2024; implementing regulations finalized in early 2025. Permit fee: $400 for a two-year period (biennial renewal). Owner occupancy required: at least 30 days per year. Property limit: an owner may register only ONE West Tisbury property as an STR. Minimum stay: 2 nights per reservation. Corporate ownership (LLC, trust) permitted only if all members are natural persons. Application requires proof of owner occupancy, insurance certificate, local contact information, Building Department inspection, and Board of Health inspection. Operator must register with DOR via MassTaxConnect.

- EDGARTOWN: As of 2025, NO local STR licensing requirement. An Edgartown short-term rental committee sought authorization at the spring 2026 town meeting to spend $80,000 on a comprehensive STR study through the UMass Donahue Institute (Amherst). The town estimates roughly 1,400 STRs currently operating. Until a bylaw passes, only state DOR registration, $1M insurance, and 11.7% combined excise apply.

- OAK BLUFFS: As of 2025, NO local STR licensing requirement. A draft bylaw heading to the April 2026 town meeting proposes town registration, a 30-day annual owner occupancy requirement, and a one-property-per-owner limit. Final adoption status depends on town meeting outcome.

- CHILMARK: As of 2025, NO local STR licensing requirement. A draft bylaw heading to the spring 2026 town meeting proposes treating STRs as 'an accessory use of residential properties' with no nightly cap, no annual stay limit, and no owner-occupancy requirement (an earlier draft 95-night cap was rejected). Final adoption status depends on town meeting outcome.

- AQUINNAH (formerly Gay Head): As of 2025, NO local STR licensing requirement; the town has the smallest year-round population on the Vineyard.

COMMUNITY IMPACT FEE (optional, town-by-town). Under MGL c.64G s.3D, a city or town that has adopted the local room occupancy excise may also adopt a community impact fee of up to 3% on transfers of occupancy of (a) a 'professionally managed unit' (operator has 2 or more units in the same town) or (b) a short-term rental that is not the operator's primary residence and is in a 2- or 3-family building also owned by the operator. Tisbury's draft 2026 bylaw included a proposed tax increase on professionally-managed rentals from 6% to 9% (effectively adding the 3% community impact fee).

MARTHA'S VINEYARD COMMISSION (DRI REVIEW). Under MGL c.831 of the Acts of 1977 (the MV Commission enabling act, as amended), the Martha's Vineyard Commission reviews 'Developments of Regional Impact' (DRIs). Standard residential STR operations in existing dwellings do NOT trigger DRI review; DRI thresholds apply to large-scale new lodging, multi-unit development, or substantial expansion. Hosts converting an existing single-family or accessory dwelling unit for STR use generally do not require MVC review.