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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

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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

63º
4.69
74º
1.87
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3.03
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
75º 19º
2.06
59º -2º
1.97
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This climate histogram shows you the weather patterns in Gloucester. The warmest months in Gloucester are July and August, when temperatures reach 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

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Homeaway, VRBO and more. Gloucester has 2212 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 $25 per night. A typical accommodation in Gloucester costs on average $332 per night.

If you need an internet connection during your stay in Gloucester, then you can choose from over 650 places to stay that provide WiFi internet. We have 54 accommodations that come with a breakfast included. Choose from 12 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Gloucester? Then choose one of the 592 places to stay that comes with a parking spot included. 8 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 160 pet-friendly accommodations available.

We combine a wide variety of Gloucester accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 418 places to stay from Airbnb, 146 accommodations from Homeaway and 94 places to stay from VRBO.

1276 accommodations in Gloucester have been reviewed: 65% are rated excellent or good. 820 places to stay in are instantly bookable.

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