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 offers a delightful blend of beach and outdoor activities, making it an ideal destination for a scenic getaway. Visitors can enjoy music concerts, explore local arts centres, and participate in educational experiences. Weekend getaways can be enhanced with walking tours, exciting adventures, and a plethora of attractions, alongside seasonal activities that cater to diverse interests.

Shopping

For unique gifts, visit Bewitched in Salem, 20.9km from Gloucester. You can also explore Todd Farm Flea Market, a lively spot for various treasures, also 20.9km away. If you're up for a drive, MarketStreet Lynnfield, 32.2km from Gloucester, offers a vibrant shopping experience with entertainment options.

Recreation

Immerse yourself in soothing melodies at the Shalin Liu Performance Center, just 6.4km from Gloucester. Enjoy captivating performances at the Gorton Theatre, perfect for a romantic evening. For relaxation, explore the serene Halibut Point Reservation, where nature rejuvenates the spirit and fosters wellness.

Adventure

Embark on an exhilarating adventure with Capt Bill & Sons Whale Watch, where you can marvel at magnificent whales in their natural habitat. For a scenic hike, explore Dogtown’s picturesque trails surrounded by lush landscapes. For family fun, visit the Water Park of New England, a short drive from Gloucester.

Nightlife

Gloucester's nightlife offers a relaxed yet vibrant atmosphere. Visit Park-9 Dog Bar, a charming drinking pub 40.2km away, where you can unwind with craft drinks in a romantic setting and enjoy lively entertainment vibes throughout the evening.

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

Find the best attractions near Gloucester

Gloucester, Massachusetts, is perfect for beach lovers and outdoor enthusiasts, offering a blend of scenic beauty and rich history. Key attractions include the Gloucester Cathedral, Gloucester Docks, and the vibrant Gloucester Quays. Visitors can enjoy the local parks and explore historic houses and museums, making it an ideal destination for those seeking culture and relaxation by the sea.

  • Long Beach: Experience the quintessential beach vibes at Long Beach, located 4.8km from Gloucester. This beautiful stretch of sand offers a perfect spot for sunbathing, swimming, and beachcombing, ensuring a relaxing day by the sea.
  • Peabody Essex Museum: Immerse yourself in culture at the Peabody Essex Museum, situated 14.8km away. This renowned art museum features an impressive collection of Asian art, maritime artifacts, and American decorative arts, making it a cultural treasure trove.
  • Cape Ann: Discover stunning scenery at Cape Ann, located 6.4km from Gloucester. This picturesque cape boasts rugged coastlines, charming fishing villages, and scenic beaches, offering ample opportunities for exploration and relaxation.

Best time to go to Gloucester

The best time to visit Gloucester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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! (924 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 S$305 per night from 9 Feb to 10 Feb
S$305
9 Feb - 10 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
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is S$133 per night from 23 Feb to 24 Feb
S$133
23 Feb - 24 Feb
includes taxes & fees
8/10 Very Good! (2,390 reviews)
Clean room. Friendly staff. Would stay again!

Reviewed on 31 Jan, 2026

DoubleTree by Hilton Boston North Shore
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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.