Gloucester Holidays

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Top Flight + Hotel Deals in Gloucester

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

Downtown Boston
€798
per person
26 Nov - 29 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Nice place. Centrally located. N

Reviewed on 22 Sept 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
€2,002
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,317 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
€3,337
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.

Reviewed on 22 Sept 2026

Raffles Boston

Raffles Boston

Back Bay
€2,809
per person
27 Oct - 3 Nov
found 12 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children. For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience. To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning. What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before. Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special

Reviewed on 21 Sept 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

Back Bay
€2,604
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.2/10 Wonderful! (2,454 reviews)

Where to stay in Gloucester

Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

East Gloucester

2 out of top 10 points of interest in this area

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

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A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

Downtown Gloucester

3 out of top 10 points of interest in this area

While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Maritime Gloucester.

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A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

While Rocky Neck isn't home to many top sights, Rocky Neck Art Colony and Maritime Gloucester are some notable places to visit nearby.

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A coastal landscape with a lighthouse, rocky shoreline, and a beach.

Annisquam

Though Annisquam may not have many top sights, you can venture to the surrounding area to see attractions like Wingaersheek Beach and Plum Cove Beach.

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A garden with purple flowers and a foggy coastline.

Magnolia

You'll enjoy the beaches and restaurants in Magnolia. You might want to make time for a stop at Gray Beach or Massachusetts Bay.

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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

141 Essex Avenue Gloucester MA
€204
4 Oct - 5 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"This place was awesome. The service was fantastic at Check In. Great view from my room super clean, comfortable beds a very relaxing stay"

Reviewed on 21 Sept 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
€276
30 Sept - 1 Oct
includes taxes & fees
Beauport Hotel Gloucester
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

138 Eastern Avenue Gloucester MA
€169
24 Sept - 25 Sept
includes taxes & fees
9.2/10 Wonderful! (492 reviews)
"Very clean and friendly place"

Reviewed on 21 Sept 2026

Sea Lion Motel and Cottages
See all 1,873 properties in Gloucester
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

A beach with a lifeguard tower, houses in the background, and the ocean.

Good Harbor Beach

9.2/10 (191 reviews)
Stroll along Good Harbour Beach's pristine white sands, walking to Salt Island at low tide. Reserve summer parking in advance to enjoy this Atlantic gem with its gentle surf and family-friendly atmosphere.
See properties
A clear lake with visible rocks and a distant shoreline with houses.
Photo by The Curious Zephyr

Wingaersheek Beach

9.4/10 (83 reviews)
This pristine beach captivates with white sands, clear shallow waters, and dramatic rock formations. Visit at low tide to explore expansive sandbars and discover hidden tide pools teeming with marine life.
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A stone archway with a view of the sea.

Hammond Castle

9.4/10 (86 reviews)
Explore this 1920s medieval-style castle built by inventor John Hays Hammond Jr. on Massachusetts' coast. Wander through grand halls filled with Roman and Renaissance artefacts while enjoying dramatic ocean views.
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A museum exhibit with a large wooden boat and a painting titled 'Out o' Gloucester'.

Cape Ann Museum

9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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A coastal town with rocky shores, a prominent church, and a clear blue sky.

Stage Fort Park

9.2/10 (71 reviews)
After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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A bustling harbor with a red building, a maritime heritage center sign, and a crowd of people.

Maritime Gloucester

9.4/10 (63 reviews)
Maritime Gloucester showcases the oldest operating marine railway in the US alongside interactive exhibits of local marine life. Explore the historic Dory Shop or sail the harbour aboard the traditional Schooner Ardelle.
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A beach with clear water, sandy shore, and green foliage.

Half Moon Beach

9.0/10 (45 reviews)
This crescent-shaped cove offers calm waters and golden sand within historic Stage Fort Park. Explore the rocky cliffs for picturesque views of Gloucester Harbour while enjoying the tranquil atmosphere.
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A coastal scene with clear blue water, rocky shoreline, and several sailboats anchored in the distance.

Niles Beach

8.0/10 (8 reviews)
This serene harbour beach offers calm waters and gentle waves perfect for families with young children. Visit at sunset to witness breathtaking golden light while collecting sea glass along the shore.
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What to do in Gloucester

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

€15
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

€19
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

€15
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester holiday package cost?
Offering great value package deals from €798 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.

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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.