Gloucester Vacation Packages

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Your Gloucester Vacation

Say farewell to the worries of planning and hello to a Gloucester vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is great for walking, nature and views. Eager to explore your new surroundings? Cape Ann, Good Harbor Beach and Wingaersheek Beach are just a few of the leading places to visit during a trip to Gloucester. No matter your travel plans or the size of your budget, organizing a tailored Gloucester vacation is a cinch with Expedia.

Top Gloucester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
Boston Harbor Hotel
The Langham, Boston
The Inn at Hastings Park, Relais & Chateaux - Boston
Global Luxury Suites East Boston

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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 vacation experience with its stunning beaches and outdoor scenery. Visitors can enjoy various activities, including boat trips, golf vacations, and shore excursions. The local arts centre hosts music concerts, providing a vibrant cultural scene, while shopping excursions allow for unique finds. Whether you're looking to relax on the beach or explore the scenic beauty, Gloucester has something for everyone.

Shopping

In Gloucester, visit Oldies Marketplace for unique finds. If you're up for a drive, check out Todd Farm Flea Market for a lively atmosphere. MarketStreet Lynnfield offers a larger shopping experience with entertainment, family-friendly options, and a variety of stores, located a bit further away.

Recreation

Explore Waterfront Promenade Park for serene walks along the waterfront, perfect for relaxation. Enjoy live performances at the Shalin Liu Performance Center, where music fills the air. The Gorton Theatre offers captivating shows, creating a delightful cultural experience for families and couples alike.

Adventure

Experience thrilling water slides and lazy rivers at the Water Park of New England, located 25.7km from Gloucester. Enjoy exhilarating whale watching with Capt Bill & Sons, offering outdoor excitement. Explore scenic trails and breathtaking views while hiking Dogtown, right in Gloucester's beautiful surroundings.

Nightlife

For a lively evening in Gloucester, visit the Park-9 Dog Bar, a vibrant drinking pub located 40.2km away. Enjoy the entertainment and romantic vibes as you sip on your favourite beverage and soak in the friendly atmosphere with fellow patrons.

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

Find the best attractions in and around Gloucester

Gloucester, Massachusetts, is perfect for a beach and outdoor getaway, offering stunning scenery and rich culture. Visitors can explore beautiful beaches, historic houses, and fascinating museums, all of which provide a unique blend of relaxation and cultural experiences. Whether you're looking to soak up the sun or delve into local history, Gloucester has something for everyone to enjoy during their vacation.

  • Wingaersheek Beach: Enjoy the stunning views and serene atmosphere at Wingaersheek Beach, known for its soft sands and gentle waves, perfect for sunbathing and leisurely strolls along the shoreline. Experience the true essence of beach vibes in a picturesque setting.
  • Hammond Castle: Step into a world of romance and culture at Hammond Castle, an enchanting structure that blends medieval architecture with the scenic beauty of Gloucester. Explore its intriguing history and lovely gardens, making it a perfect spot for a romantic outing.
  • Salem Witch Museum: Located 20.9km from Gloucester, the Salem Witch Museum offers a captivating dive into the history and culture of the infamous witch trials. Engaging exhibits bring the past to life, making it a must-visit for history enthusiasts.

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 Vacation

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester vacation. 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 vacation homes are another top choice for people planning a vacation 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 vacation deals, you can see more impressive attractions like these.

Ready to book your vacation to Gloucester?

 

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Gloucester Hotel Deals

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
9.6/10 Exceptional! (936 reviews)
The hotel was perfect, we loved everything about it !!

Reviewed on Mar 9, 2026

Beauport Hotel Gloucester
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
8.4/10 Very Good! (1,000 reviews)
The room was clean, but the outside of the building our room was in, behind the inn, was run down and the back of the inn was in disrepair. Not a very pleasant experience.

Reviewed on Jan 19, 2026

Castle Manor Inn
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 CA $295 per night from Mar 15 to Mar 16
CA $295
CA $329 total
Mar 15 - Mar 16
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 Jan 20, 2026

The Hotel at Cape Ann Marina
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.