Destination Photo

Gloucester Vacation Rentals

Our Favorite Vacation Rentals in Gloucester

Gloucester Vacation Rentals with a Pool

Gloucester Vacation Rentals with Wi-Fi

Gloucester Pet-Friendly Vacation Rentals

Gloucester Travel Guide

Gloucester is the oldest seaport in the United States and it has also become a summer vacation destination for family fun. As part of the Massachusetts’ North Shore, this city boasts lots of stunning beaches and a picturesque harbor, with lots of opportunity for boating, swimming, and fishing. The Main Street in Gloucester is home to boutiques and local stores, as well as restaurants to enjoy in the evening. In particular, waterfront dining is popular, with beautiful views of the harbor with a fine dining experience. Local and fresh seafood is always top of the menu in Gloucester.

Things to Do in Gloucester

Gloucester is home to some fantastic beaches to explore. This includes Wingaersheek Beach, which is a popular place to paddle and go beachcombing. The water is clean and the sand is pristine. Good Harbor Beach is another favorite spot for locals and visitors alike, with beautiful white sand and blue sea. This is where to go when the sun is shining. For stunning harbor views, head to Stage Fort Park and Beach. To view a historic home in Gloucester, head to the Sleeper-McCann House. This is a stunning mansion and visitors can tour the rooms of this designer. The Cape Ann Museum is also a place to learn about the area’s past and the roles of fishing and shipping in town.

Best Time to Visit Gloucester

The summer is the most popular time to vacation in Gloucester.

Price and Availability in Gloucester

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The most expensive month to stay in a vacation rental in Gloucester is in August, while the cheapest month is in April. The most popular time to book a vacation rental in Gloucester is in the high season in August. Gloucester has its low season in January, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Gloucester tends to be Sunday, while the most expensive day tends to be Thursday. Vacation homes in Gloucester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Gloucester

96º 52º
3.46
94º 53º
4.79
93º 45º
5.76
83º 25º
4.88
69º 12º
10.2
62º 15º
2.97
62º -4º
2.07
76º
3.89
62º 13º
5.09
69º 24º
4.85
89º 37º
1.73
88º 48º
3.43
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in Gloucester. The hottest month in Gloucester is June, when temperatures peak at 96 ˚F. The coolest month is January, when temperatures drop to -4 ˚F. The wettest month in Gloucester is November with 10.2 inches of rain, while the driest month is May with 1.73 inches of rain.

What Expert Travelers Think

Destinations near Gloucester