Gloucester Holidays

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Where to stay in Gloucester

Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester

Things to do in and around Gloucester

Gloucester, Massachusetts, offers a delightful blend of beach relaxation and outdoor adventure, making it an ideal destination for a scenic getaway. Visitors can enjoy music concerts, explore an arts centre, and embark on walking tours. With a variety of exciting attractions and seasonal activities, Gloucester is perfect for weekend escapes and memorable experiences in a charming coastal setting.

Shopping

For a unique shopping experience, visit Todd Farm Flea Market, offering a variety of local goods, just 20.9km from Gloucester. If you're up for a drive, explore MarketStreet Lynnfield, 32.2km away, where you'll find a mix of shops, entertainment, and dining options for the whole family.

Recreation

Waterfront Promenade Park offers a peaceful retreat with scenic views, perfect for relaxation and leisurely strolls. The Shalin Liu Performance Center provides an enchanting atmosphere for enjoying live music, while The Gorton Theatre showcases captivating performances, making it ideal for families and couples seeking cultural enrichment.

Adventure

Experience the thrill of Capt Bill & Sons Whale Watch, where you can embark on an exhilarating adventure to observe majestic whales in their natural habitat. For a scenic hike, explore Dogtown's trails, offering stunning views and a taste of Gloucester's natural beauty. For family fun, visit the Water Park of New England, located 25.7km away, featuring exciting rides and attractions.

Nightlife

A night in Gloucester offers a lively atmosphere, especially at the Park-9 Dog Bar, a delightful drinking pub 40.2km away. With its romantic vibe and entertainment options, it's the perfect spot to unwind and enjoy the local nightlife scene.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Gloucester

Gloucester, Massachusetts, is an idyllic destination for beach lovers and outdoor enthusiasts alike, offering a wealth of cultural experiences. Visitors can explore the Gloucester Museum, stroll along the picturesque docks, and admire the historic Gloucester Cathedral. With its charming parks and local attractions, Gloucester presents a delightful blend of scenic beauty and rich history, making it the perfect spot for a memorable holiday.

  • Wingaersheek Beach: Experience the serene beauty of Wingaersheek Beach, where soft sands meet gentle waves. It's a perfect spot for relaxation, beachcombing, and enjoying stunning sunsets over the Atlantic Ocean.
  • Maritime Gloucester: Dive into the maritime heritage of Gloucester at Maritime Gloucester. This engaging museum showcases local history, shipbuilding, and fascinating exhibits, making it a cultural gem for visitors seeking to understand the region's seafaring past.
  • Stage Fort Park: Enjoy the great outdoors at Stage Fort Park, a family-friendly urban park featuring playgrounds, picnic areas, and scenic views of the harbour. It's an ideal place for leisurely strolls, outdoor activities, and soaking in the local atmosphere.

Best time to go to Gloucester

The best time to visit Gloucester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Gloucester falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Gloucester falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.1°F (-0.5°C)Light RainMostly SunnyModerately LowSlightly Low
February31.8°F (-0.1°C)Light RainMostly SunnyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
April45.1°F (7.3°C)Light RainMostly SunnyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageSlightly High
June62.4°F (16.9°C)Light RainMostly SunnyModerately HighAverage
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighAverage
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighAverage
September64.0°F (17.8°C)Light RainMostly SunnyAverageSlightly High
October55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly High
November45.1°F (7.3°C)Light RainMostly SunnyModerately LowAverage
December37.4°F (3.0°C)Light RainMostly SunnyModerately LowSlightly Low

Tips to save on your trip to Gloucester

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Gloucester.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Gloucester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Gloucester Beach Holiday

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester holiday. If you're eager to save on your trip to Gloucester, we'll let you in on a secret — choose one of our Gloucester packages. Grab one close to Pavilion Beach, only 0.32 kilometres from the city centre and a must-do while here. Alternatively, select a package that puts you closer to Cressy Beach, another gorgeous coastline. Whichever you choose, you'll be left with extra dollars in your travel budget to have fun with.

Things You Should Know About Gloucester

  • Drift off to sleep to the gentle sounds of the sea in one of our Gloucester beach hotels. Nothing beats staying with walking distance of the ocean.
  • Private holiday homes are another top choice for people planning a holiday in Gloucester. Some great examples are Castle Manor Inn and The Hotel at Cape Ann Marina.
  • Roughly 29,800 people reside in Gloucester. If you want some tips about things to see and do here, why not start a conversation with some of the friendly locals? Our Gloucester things to do page is also a handy source of information.
  • Don't head home without exploring Cape Ann, Capt Bill & Sons Whale Watch and Dogtown. With the cash you save through our Gloucester holiday deals, you can see more impressive attractions like these.

Top hotels in Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
9.6/10 Exceptional! (923 reviews)
Everything and everyone was top notch

Reviewed on 2 Feb 2026

Beauport Hotel Gloucester
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue Gloucester MA
Fully refundableReserve now, pay when you stay
The price is €203 per night from 19 Feb to 20 Feb
€203
19 Feb - 20 Feb
includes taxes & fees
8.4/10 Very Good! (780 reviews)
The rooms are fresh and spotlessly clean. Great views of the Annisquam River. Nice location outside of town. The staff was fantastic. We love the marina vibe. We stayed in January when the restaurant is only open a couple of days a week - we'll hit that up next time. We dined nearby at The Causeway ...

Reviewed on 20 Jan 2026

The Hotel at Cape Ann Marina
Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!

Gloucester MA
9.6/10 Exceptional! (50 reviews)
We enjoyed our stay! Cottage was comfy and cozy!

Reviewed on 18 Oct 2025

Luxury 1900's romantic retreat steps from the beach - King Suite!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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What to do in Gloucester

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.