Where we work · Gloucester
Gloucester vacation rental management.
Gloucester is a working seaport and a year-round community. We manage homes across the city because we live here, we know the neighborhoods, and we genuinely love it.
On the calendar
Twelve months, more or less.
January through April are the quiet months here. The rest of the year, Gloucester rents steadily. Fall can be the surprise: October tends to be strong thanks to the weather and the overflow from Salem during Halloween season. Salem's short-term rental rules are tight, so weekend visitors head north into Gloucester and Rockport.
The calendar has more peaks than most people realize. St. Peter's Fiesta in late June. Juneteenth weekend. Schooner Festival over Labor Day. Harvest Fest in October. We plan around each one rather than reacting to them.
“We live here. That is the whole pitch, and it is most of the advantage.”
By neighborhood
Gloucester by neighborhood.
Nine distinct pockets of the city. Here's why we love each one.
Rocky Neck
America's oldest working art colony. We have friends in the galleries, and it's where we take visitors first.
East Gloucester & Bass Rocks
Niles Beach at sunset, Bass Rocks Golf Club, the Atlantic Path. The east shore reads like a postcard and then some.
Good Harbor
The best beach on the North Atlantic, in our opinion. Thirty minutes down the road and feet in the sand.
Magnolia
The village feels like it stopped time around 1965. Lobster shacks, a main street, a beach on the sound.
Annisquam
The river and the village feel like Maine on a quieter day. The lighthouse at sunset is a real thing.
Wingaersheek & West Gloucester
Flat water, sheltered tide pools. Wingaersheek is where we go on a day off in August.
Downtown
St. Peter's Square, Main Street, the working waterfront. We're here twice a week for one reason or another.
Lanesville
Quiet, a little rural, people nod when you drive past. Folly Cove, the granite quarries, Cape Ann at a different tempo.
Eastern Point
The lighthouse, the Dog Bar Breakwater, the walk out to the end on a clear day. A treasured tip of the city.
Questions worth asking a person
Gloucester's short-term rental rules.
Every owner's situation is a little different, and the rules do change. Rather than have this page try to be the authority, text or email us the specifics of your home. We'll walk you through what applies and what doesn't.
Keep exploring
Our full service area
The Cape Ann overview: the ten-minute ring, the coastline, every town we cover.
How we manage each home
Design and set-up, daily pricing, guest care, turnovers, and monthly reporting, end to end.
Meet Allie and Ryan
The two Massachusetts natives who own and run Rising Tide, both based in Gloucester.