Gloucester Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Gloucester

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
Boston Harbor Hotel
The Newbury Boston
Raffles Boston
The Langham, Boston

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

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is €208 per night from 10 Nov to 11 Nov
€208
10 Nov - 11 Nov
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"I loved the room with a view of the water. It was clean with plenty of room. Parking in front of the room was convenient. We had a late check-in which went smoothly. What I didn't like was our power going out twice. Only our room, which means it wasn't a general power outage. When we reported it ..."

Reviewed on 5 Nov 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is €212 per night from 8 Nov to 9 Nov
€212
8 Nov - 9 Nov
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Beauport rang all the bells for understated North Shore Elegance. Meals( lunch & drinks were delish) Afternoon 10/27 server was a gem. ( local lady who provided helpful tips & is a single Mom so hope you can identify her.) Very Clean room. Comments: my ocean view rm selection On reserving, yielded ..."

Reviewed on 5 Nov 2026

Beauport Hotel Gloucester
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue Gloucester MA
9.2/10 Wonderful! (514 reviews)
"Good hotel"

Reviewed on 7 Nov 2026

Sea Lion Motel and Cottages
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.

Stay near popular Gloucester attractions

What to do in Gloucester

Frequently asked questions

How much does a Gloucester holiday package cost?
Offering great value package deals from €3,895 on Expedia, you'll be thrilled with how little a holiday to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester holiday packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester holiday. With a well-organised schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
How to find the best Gloucester package deals?
Use Expedia's filters to find some great Gloucester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Gloucester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Gloucester holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Gloucester?
If you're considering a spontaneous Gloucester getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Gloucester?

  1. Choose your dates: What you'd like to do in Gloucester and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you're up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

Explore a world of travel with Expedia

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