Gloucester Vacation Rentals
1-12 of 12 rentals
Related destinations
About Gloucester
Experience one of the small coastal towns that make up the heart of New England by paying a visit to Gloucester, MA. 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.
With an active commercial fish pier, historic downtown area, and amazing seafood, this welcoming town offers plenty 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.
History of Gloucester, MA
With a history dating back to 1623, the town we know as Gloucester (pronounced "gloster") has a long and storied 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.
The first pioneers made land at Half Moon Beach and set up fishing stages in the area now known as Stage Fort Park, where you can go explore and check out the memorial boulder that sits in the park today.
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.
The first pioneers made land at Half Moon Beach and set up fishing stages in the area now known as Stage Fort Park, where you can go explore and check out the memorial boulder that sits in the park today.
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.
Things to Do in Gloucester, MA
The historic sights keep on coming when you visit Gloucester, although some are a bit more recent. The breathtaking Hammond Castle sits along the rocky shoreline about four miles from town, making it a great daytime outing to explore the history and amazing artifacts inside. This medieval-style castle was built in 1929 by John Hammond, one of America's premier inventors of the early 20th century.
If you're looking for something a bit more laid-back, Gloucester has several local beaches that are great for swimming and playing in the sand. Head over to Good Harbor Beach or Wingaersheek Beach for a fun day in the sun (or a windy stroll, depending on the season!).
If you're looking for something a bit more laid-back, Gloucester has several local beaches that are great for swimming and playing in the sand. Head over to Good Harbor Beach or Wingaersheek Beach for a fun day in the sun (or a windy stroll, depending on the season!).
Day Trips from Gloucester, MA
For a cool day trip, head north to the town of Salem, the site of the infamous Salem Witch Trials. Sign up for a tour through the Witch House and the Dungeon Museum, then go for a stroll through the Salem Witch Trials Memorial.
While this town becomes very popular come Halloween time, it offers interesting Colonial history, beautiful old buildings, and great antiquing nearby. Any literature and history lovers should take a tour through the beautiful House of the Seven Gables to learn about Nathaniel Hawthorne's legacy, Salem's maritime history, and discover a hidden staircase. Be sure to stop by the impressive Stickworks Statue for a photo op before you leave.
Plan a fun getaway to one of our Gloucester vacation rentals, and enjoy a trip filled with delicious fresh seafood, amazing history, and scenic coastal sights!
Photo Credit: Amanda via Flickr