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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

62º 13º
69º 24º
89º 37º
88º 48º
96º 52º
94º 53º
93º 45º
83º 25º
69º 12º
62º 15º
62º -4º
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

Vacation Rentals in Gloucester

At AllTheRooms.com we have accommodations from all of your favourite providers - Airbnb, Homeaway, VRBO and more. AllTheRooms has 577 vacation rentals, hotels and other great places to stay during your time in Gloucester, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. A trip to Gloucester can be affordable - our lowest price accommodation is available at $28 per night. On average, a place to stay in Gloucester will cost you $338 per night.

If you want to stay connected during your trip, then you can choose from over 333 accommodations in Gloucester that have WiFi. We have 31 accommodations that come with a breakfast included. Choose from 6 places to stay that provide gym facilities, so you won't miss a single workout. If you are driving to Gloucester, you'll want to pick from 307 places to stay that provide parking. We have 4 places to stay that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 81 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 220 places to stay from Airbnb, 70 accommodations from Homeaway and 47 places to stay from VRBO.

319 accommodations in Gloucester have been reviewed: 63% are rated excellent or good. 216 places to stay in are instantly bookable.