Gloucester Vacation Rentals
Compare 9 vacation rentals.
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With a Gloucester vacation rental, you have a front-row seat to most scenic small coastal towns that make up the heart of New England. This small fishing town rests along the eastern end of Cape Ann, near the larger town of Rockport and about 40 miles from the city of Boston. Experience beachside bliss and relaxation on your next trip to Massachusetts.
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Yes, 10 of our Gloucester homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).
Browse dog-friendly homes >Yes. 32 of our Gloucester vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Gloucester team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >Feel right at home on your trip to Cape Cod with Gloucester vacation rentals. With an active commercial fish pier, a historic downtown area, and amazing seafood, this welcoming town offers plenty of New England charm. Spend the day exploring the local museums and memorials, learning about the town's rich history, and head back to your vacation rental to enjoy some delicious fresh lobster or oysters.
Between a bike ride along the shore and kicking your feet up to watch the waves come in, there’s no shortage of things to do near Gloucester.
With a history dating back to 1623, the town we know as Gloucester (pronounced "gloster") has a long and interesting background. The area was originally founded at Cape Ann by a group of settlers from Dorchester, England, predating both Salem and the city of Boston.
Since many original settlers moved to Salem in hopes of finding better farmland, the area of Gloucester was briefly abandoned before slowly coming back on the map again in the late 1600s. Today, you can see a variety of local sights near your vacation rental to explore the town's history, from the Town Green where settlers built the first school, to the White-Ellery House built in 1710 for Gloucester's first minister.
