Short-Term Rental Management in Gloucester, Rockport and Cape Ann, MA

Why Guests Come to Cape Ann

• The beaches. Gloucester's Good Harbor Beach, Wingaersheek Beach and Stage Fort Park are the summer draw. The city requires non-resident beachgoers to reserve parking in advance, and resident stickers cover the lots, so your guests count as non-residents and need to book.
• St. Peter's Fiesta. Gloucester's five-day fiesta ran June 24 to 28 in 2026, with seine boat races, the greasy pole contest and the blessing of the fleet.
• The Gloucester Schooner Festival. Maritime Gloucester's festival filled the harbor with schooners from September 3 to 6, 2026, over Labor Day weekend, with a parade of sail and fireworks.
• Rockport's music season. The Rockport Chamber Music Festival ran June 12 to July 12, 2026 at the Shalin Liu Performance Center.
• Getting here without a car. Rockport is the end of the MBTA Newburyport/Rockport commuter rail line, with Gloucester stops on the way, which suits guests coming from Boston.

The Cape Ann Rental Year

Summer is the core season: beach weekends from late June through Labor Day, with St. Peter's Fiesta and July music weeks in the middle. September has the Schooner Festival. October brings leaf-peepers and visitors spilling over from Salem's Halloween month. Winter is quiet, with weekend demand from couples and remote workers, so pricing has to drop and minimum stays usually shorten. Our seasonal pricing guide explains how to set up those shifts.

Short-Term Rental Rules on Cape Ann

Gloucester

Gloucester regulates short-term rentals through Article V of Chapter 5 of its Code of Ordinances (sections 5-63 to 5-69), adopted in 2024 and amended in 2025. As of October 2026 it says:

• Annual permit from the Inspectional Services Department for any home offered more than 15 days a year. Permits run January 1 to December 31, and renewals are due by December 1.
• Fees: $100 for a shared unit (rooms in your home while you are there), $150 for your primary residence, $300 for a non-primary unit.
• Non-primary homes: rentals capped at 120 days a year in aggregate, one non-primary permit per operator, and no more than 500 non-primary permits citywide. A primary residence (lived in at least six months of 12) may be rented for six months.
• Existing units: homes that held a valid DOR Certificate of Registration on the article's April 1, 2025 effective date are exempt from the one-unit, primary-residence and 120-day limits, but not from the rest of the article.
• Occupancy and use: two guests per bedroom plus two more, one party at a time, no stays under ten hours, and no weddings or private functions.
• Ownership: no corporate-owned units. An LLC or trust qualifies only if every member is a natural person.
• Posted information: trash and recycling schedule, parking rules (resident-only zones, street sweeping, snow emergencies), the noise and animal control ordinances, and the locations of gas shutoffs, exits, alarms and extinguishers.
• Penalty: $400 per occurrence, and each day counts as a separate offense.

The city's guidelines page adds a safety checklist covering egress, smoke and CO alarms and hot water.

Rockport

Rockport voters adopted a short-term rental bylaw, Chapter 276 of the town code, at the April 5, 2025 Annual Town Meeting. It took effect January 1, 2026. It applies to stays of fewer than seven consecutive nights and requires a license from the Select Board, renewed every calendar year. You must name a local agent who can act when you are not there and keep a guest registry, and the home can be inspected by the Health, Fire and Inspectional Services departments. The Select Board sets the license fee each year; ask Town Hall at 978-546-5000 for the current amount. Separately, Rockport's Board of Health licenses and inspects pools at short-term rentals.

Rockport is also a state "Seasonal Community." The state designated it on February 28, 2026, and voters accepted the designation at the 2026 Annual Town Meeting. That opens the door to year-round housing bylaws, so watch for new rules.

Local Room Taxes

The Division of Local Services databank (read 6 October 2026) lists a 6% local room excise in Gloucester (since April 2010) and Rockport (since January 2012). Both towns also charge a 3% community impact fee on professionally managed units and owner-occupied two- and three-family homes. Neighboring Essex lists 6% and Manchester-by-the-Sea 3%, with no impact fee in either. State registration, the 5.7% state excise and the $1 million insurance rule are on our Massachusetts short-term rental laws page and room occupancy tax page.

Running a Rental on Cape Ann

• Trash. On October 1, 2026, Gloucester began automated cart collection with Casella, replacing the Purple Bag program. Put the new schedule in your guest binder. The ordinance says carts go out no earlier than 4 p.m. the day before pickup.
• Parking. Old Gloucester streets and Bearskin Neck have little parking. List the exact number of spaces, and tell guests about resident-only zones and the beach parking reservations.
• Winter. Snow emergencies restrict on-street parking. Plan plowing and shoveling before you take January bookings.
• Pools. In Rockport, a pool at a rental needs a Board of Health license.

How New England Host Co Works on Cape Ann

New England Host Co covers Massachusetts statewide, and today we manage homes in the Worcester area. Every home we take on has to be within 45 minutes of the base its cleaning and maintenance crew works from, so send us your Cape Ann address and we will confirm. Under full-service management, a local crew handles housekeeping and an inspection after every stay, and we review pricing daily in PriceLabs. Permit and license fees stay with the owner. Ask for a free property analysis on our contact page or at (978) 672-4578. For other towns on this coast, see North of Boston.

FAQ

Can I Rent My Gloucester Second Home All Summer?

Not as a new permit. A non-primary home is limited to 120 rental days a year, and you can hold only one non-primary permit, unless the home had a DOR certificate on April 1, 2025, which exempts it from those limits. The city caps non-primary permits at 500.

Does Rockport Require a License If I Only Rent by the Week?

No. Rockport's bylaw covers stays of fewer than seven consecutive nights. You still register with the state and collect state and local room tax on stays of 31 days or less.

What Is the Total Room Tax in Gloucester?

As of October 2026: 5.7% state plus Gloucester's 6% local excise. A 3% community impact fee applies only to professionally managed units and to owner-occupied two- and three-family homes. Airbnb collects these on its bookings.

Who Do I Call in Rockport?

Rockport Town Hall, 34 Broadway, at 978-546-5000. The Select Board issues short-term rental licenses.

This page is general information as of October 2026, not legal or tax advice.