Gloucester Holidays

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Your Gloucester Holiday

Say farewell to planning hassles and hello to a Gloucester holiday package. With your travel details organised before you go, you can focus on discovering the best of this city, starting with Great Neck, which is good for walking, nature and views. A trip to Gloucester is a terrific opportunity to do some sightseeing. Be sure to stop by big-name attractions such as Good Harbour Beach, Cape Ann and Hammond Castle. Browse Expedia's extensive range of travel options and start organising your dream holiday to Gloucester now.

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.

Gloucester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
29,800
Max Temp Winter
2ºC
Max Temp Summer
21ºC
Top Sights
Good Harbour Beach, Hammond Castle and Wingaersheek Beach

Our pick of the best Gloucester Hotel Deals

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is AU$277 per night from 28 Aug to 29 Aug
AU$277
28 Aug - 29 Aug
includes taxes & fees
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
The price is AU$361 per night from 16 Sept to 17 Sept
AU$361
16 Sept - 17 Sept
includes taxes & fees
8.2/10 Very Good! (725 reviews)
Lovely Getaway
"The staff was great, our room was lovely. Had dinner at Mile Marker 1, and it was delicious with a great view."

Reviewed on 15 Aug. 2025

The Hotel at Cape Ann Marina
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is AU$297 per night from 1 Sept to 2 Sept
AU$297
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (412 reviews)
"Room was very clean, the shower was hot with water pressure and bed was comfortable. Win, win, win!"

Reviewed on 22 Aug. 2025

Sea Lion Motel and Cottages
See all 1,764 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Gloucester

Plum Cove Beach

If a restful holiday is part of your travel plans, Plum Cove Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

Plum Cove Beach

Ravenswood Park

Explore the great outdoors at Ravenswood Park, a lovely green space in Gloucester. Wander the beautiful beaches and seaside in the area.

Ravenswood Park

What to do in Gloucester

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

AU$77
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

AU$26
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

AU$26
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 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.

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