Gloucester Holidays

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Top Flight + Hotel Deals in Gloucester

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

South End
€1,066
per person
3 Oct - 8 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,783 reviews)
Everything is good

Reviewed on 8 Aug 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
€2,250
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
.

Reviewed on 9 Aug 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
€2,891
per person
23 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
It was our first visit to Boston. So glad we stayed at the Four Seasons on Boylston. It’s centrally located to all the attractions that were on our list. The city view trolley is located across the street from the hotel. Easy hop on and off. Staff were amazing - friendly and professional. We will definitely stay here again when we come back to Boston.

Reviewed on 6 Aug 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

Downtown Boston
€1,448
per person
3 Oct - 8 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (5,158 reviews)
Great hotel. Busy area but great location to walk all of Boston from Back Bay to Waterfront. Entire staff from check in to valet to housekeeping friendly and helpdul

Reviewed on 8 Aug 2026

The Newbury Boston

The Newbury Boston

Back Bay
€2,349
per person
3 Oct - 8 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (695 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

3 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.

Gloucester MA Fishermens Memorial

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 Capt Bill & Sons Whale Watch.

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.

Annisquam lighthouse in Massachusetts

Rocky Neck

While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.

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.

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
€202
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"When I booked the place, I thought we were staying in the house. We were put in a hotel room that was nicely decorated and clean. But, small. It met our needs. We felt that the outside really needs some maintenance."

Reviewed on 9 Aug 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
€404
9 Sept - 10 Sept
includes taxes & fees
9.6/10 Exceptional! (996 reviews)
"Absolutely beautifully decorated, clean and we felt like we were on a resort especially with the pool on the roof top with a bar and music."

Reviewed on 6 Aug 2026

Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

107 Atlantic Rd Gloucester MA
€296
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (855 reviews)
"Very nice stay"

Reviewed on 8 Aug 2026

Ocean House Hotel at Bass Rocks
See all 1,872 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 rocky shoreline with large boulders and calm water.

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.
See properties
A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

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 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.
See properties
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 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 group of people in naval uniforms on a wooden deck, with a ship's rigging and a clear blue sky in the background.

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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An art gallery with wooden flooring and paintings on the walls.

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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Capt Bill & Sons Whale Watch

8.2/10 (12 reviews)
Join marine experts on a 4-hour adventure to spot humpback, fin, and minke whales in their natural habitat. Naturalists from the Blue Ocean Society provide fascinating insights while you cruise the waters off Gloucester.
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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 €1,066 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.