We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Gloucester 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 Index 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

The most expensive month to stay in a vacation rental in Gloucester is in August, while the cheapest month is in January. 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 Monday, while the most expensive day tends to be Friday. Vacation homes in Gloucester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The weather in Gloucester

75º 19º
2.06
59º -2º
1.97
63º
4.69
74º
1.87
63º
4.69
88º 29º
7.65
94º 33º
4.56
98º 48º
5.2
90º 49º
2.99
91º 48º
0.96
89º 44º
2.92
81º 33º
4.62
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days
Powered by:

This climate histogram shows you the weather patterns in Gloucester. The hottest month in Gloucester is July, when temperatures peak at 98 ˚F. The coolest month is December, when temperatures drop to -2 ˚F. The wettest month in Gloucester is April with 7.65 inches of rain, while the driest month is August with 0.96 inches of rain.

Vacation Rentals in Gloucester

Browse accommodations from all the best providers including Airbnb, Homeaway, VRBO and more at AllTheRooms.com. Gloucester has 2252 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A trip to Gloucester can be affordable - our lowest price accommodation is available at $19 per night. On average, a place to stay in Gloucester will cost you $367 per night.

If you want to stay connected during your trip, then you can choose from over 670 accommodations in Gloucester that have WiFi. 50 places to stay include a breakfast. Fitness addicts can get a workout in during their stay by choosing from 10 accommodations that have gym facilities. If you are driving to Gloucester, you'll want to pick from 608 places to stay that provide parking. 8 hotels and vacation rentals have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 158 pet-friendly accommodations available.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 5 providers in Gloucester, including 414 places to stay from Airbnb, 164 accommodations from Homeaway and 102 places to stay from VRBO

1324 of our places to stay in Gloucester have been rated by previous guests. They rated 63% as excellent or good. 812 accommodations allow instant booking.

Our providers