Gloucester Vacation Rentals, Homes, & More
Gloucester (46) Filter Cancel

1-46 of 46 Gloucester Rentals

Sort: Relevance
Your search has been expanded 20 miles to include more rentals
Loading...
LoadingLoading...

About Gloucester

Located on Cape Ann on the North Shore of Massachusetts is the city of Gloucester. This picturesque seaport city is a popular destination for people who vacation in Massachusetts, especially during the summer. Gloucester bursts with historic charm, and a great way to immerse oneself in the area’s culture and history is to stay in one of the many appealing, well-preserved Gloucester vacation rentals. 

Climate

Like most cities in Massachusetts, Gloucester experiences all four seasons and sees warm summers and cold, snowy winters. July is typically the warmest month with temperatures in the 70s, while January is usually the coldest with temperatures that can dip into the 20s. To make the most of a vacation in this part of Massachusetts, choose Gloucester vacation rentals that are available during the summer for the most pleasant stay. 

Transit

Transportation for getting around Gloucester does require some advance thought before your arrival. Driving is the easiest way to get around the area, but keep in mind the cost of parking at various attractions, such as the local beaches. To save money, park for free at Stage Fort Park and then take the Trolley Shuttle, which runs on weekends from June 15 through Labor Day. The Gloucester Water Shuttle is another great way to get as it connects Gloucester’s two Cultural Districts, Harbortown and Rocky Neck. The shuttle is only $10 to ride all day.   

Things to do

Gloucester boasts a variety of activities and attractions that are part of the allure for vacationing families in this area. The city’s beaches are some of the most popular in New England and include Good Harbor Beach, Cressey’s Beach and Wingaersheek Beach. Swimming, surfing, sunbathing, and shelling are all popular activities at Gloucester’s pristine, white-sand beaches and secluded coves. The shoreline also is home to numerous lighthouses, which are popular attractions for those staying in Gloucester vacation rentals. Some area lighthouses include Annisquam Harbor Light Station, Eastern Point Light Station, and Ten Pound Island Light.

For history buffs, the eight-foot Gloucester Fisherman’s Memorial Monument is a poignant reminder of how dangerous fishing was and it was built in memory of fishermen who lost their lives to the sea. Other historic attractions worth visiting are the Cape Ann Museum, Beauport, and the Sargent House Museum, which is located in the heart of the downtown ...

Read more