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Gloucester Vacation Rentals

Our Favorite Vacation Rentals in Gloucester

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Gloucester Vacation Rentals with Wi-Fi

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Gloucester Pet-Friendly Vacation Rentals

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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

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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 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

89º 37º
88º 48º
96º 52º
94º 53º
62º -4º
83º 25º
69º 12º
62º 15º
62º -4º
62º 13º
69º 24º
Rainy days
This climate histogram shows you the weather patterns in Gloucester. The warmest months in Gloucester are June and May, when temperatures reach 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

Browse places to stay from all the leading providers including Airbnb, Homeaway, VRBO and more at AllTheRooms.com. AllTheRooms has 572 rentals, hotels and other great places to stay while you enjoy Gloucester, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. A vacation in Gloucester can be affordable - the cheapest price rental is available at $22 per night. An average accommodation in Gloucester costs on average $331 a night.

If you need to stay connected during your trip, then you can choose from over 325 accommodations in Gloucester that have WiFi. 32 places to stay include a morning meal. You can maintain your workout regime by staying at one of 6 accommodations that provide gym facilities. If you are driving to Gloucester, you'll want to pick from 297 places to stay that provide parking. We have 4 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 78 pet-friendly places to stay in Gloucester, so if you're traveling with your pet you won't have any problems.

We combine a wide variety of Gloucester accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 219 places to stay from Airbnb, 67 accommodations from Homeaway and 43 places to stay from VRBO.

308 of the accommodations in Gloucester have been reviewed by previous guests. They rated 61% as great. 194 accommodations allow instant booking.

Destinations near Gloucester