Gloucester Holidays

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Our guide on 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.

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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 Capt Bill & Sons Whale Watch.

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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 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 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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Gloucester Holiday

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.

Our pick of the best Gloucester Hotel Deals

Castle Manor Inn

Castle Manor Inn

141 Essex Avenue Gloucester MA
NZ$380
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"Welcoming, helpful Staff. Beautiful views of the water from the balcony. Cozy, clean room. We will be back"

Reviewed on 3 Sept 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
NZ$493
17 Sept - 18 Sept
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"We had an excellent stay at the Beauport! The room was surprisingly large, clean, and well designed. The staff were very friendly and helpful. The food and drinks were great. The adults only rooftop pool was fantastic. Special shout-out to Colby for taking care of us on the rooftop. The only cons ..."

Reviewed on 3 Sept 2026

Beauport Hotel Gloucester
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

138 Eastern Avenue Gloucester MA
NZ$329
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (483 reviews)
"It was a wonderful stay. Clean and comfortable!. We look forward to staying in the future again."

Reviewed on 2 Sept 2026

Sea Lion Motel and Cottages
See all 1,881 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.
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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.
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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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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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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 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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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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What to do in Gloucester

History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

NZ$60
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Salem, MA: History and Hauntings Guided Walking Tour

Salem, MA: History and Hauntings Guided Walking Tour

NZ$60
per adult
88% of travellers recommend
Salem, MA: History and Hauntings Guided Walking Tour
Whale Watching Tour

Whale Watching Tour in Gloucester

NZ$80
per adult
98% of travellers recommend
Whale Watching Tour in Gloucester
See all activities in Gloucester

Frequently asked questions

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