Gloucester Holidays from AU$3,290
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The Latest Gloucester holiday deals
- Eurostars The Boxer
2 Oct - 7 OctEurostars The Boxer + Flight
West End5 nights4.0 star property8.8/10 - Excellent (1,527 reviews)"Eurostars has an ideal location for those that want to explore downtown Boston! The hotel was extremely clean and secure. Highly recommend!!"Reviewed July 13, 2026Return • Sydney (SYD) - Boston (BOS)SYD - BOS • 1 stop BOS - SYD • 2 stopsAU$4,400AU$3,290found 10 hours agoper traveller - The Godfrey Hotel Boston
2 Oct - 7 OctThe Godfrey Hotel Boston + Flight
Downtown Boston5 nights4.0 star property9.6/10 - Exceptional (5,118 reviews)"Liked the safety and the helpful staff"Reviewed July 16, 2026Return • Sydney (SYD) - Boston (BOS)SYD - BOS • 1 stop BOS - SYD • 2 stopsAU$4,572AU$3,476found 10 hours agoper traveller - Good Hotels Boston
2 Oct - 7 OctGood Hotels Boston + Flight
South End5 nights2.0 star property8.0/10 - Very good (55 reviews)"This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order."Reviewed May 23, 2026Return • Sydney (SYD) - Boston (BOS)SYD - BOS • 1 stop BOS - SYD • 2 stopsAU$4,273AU$3,514found 10 hours agoper traveller - The Lenox Hotel Boston
2 Oct - 7 OctThe Lenox Hotel Boston + Flight
Back Bay5 nights4.5 star property9.6/10 - Exceptional (1,615 reviews)"Great location, nice hotel and lovely staff"Reviewed July 15, 2026Return • Sydney (SYD) - Boston (BOS)SYD - BOS • 1 stop BOS - SYD • 2 stopsAU$4,628AU$3,806found 10 hours agoper traveller - Hotel AKA Back Bay
2 Oct - 7 OctHotel AKA Back Bay + Flight
Back Bay5 nights4.5 star property9.4/10 - Exceptional (1,294 reviews)Return • Sydney (SYD) - Boston (BOS)SYD - BOS • 1 stop BOS - SYD • 2 stopsAU$4,287AU$3,552found 10 hours agoper traveller
Our guide on where to stay in Gloucester
East Gloucester
If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.
Downtown Gloucester
While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.
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.
Rocky Neck
While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.
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.
Discover the most popular places to visit in Gloucester
What to do in Gloucester
History and Hauntings of Salem Guided Walking Tour
Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle
Gloucester Hotel Deals
Ocean House Hotel at Bass Rocks
Ocean House Hotel at Bass Rocks
Frequently Asked Questions
How much does a Gloucester holiday package cost?
Offering great value package deals from AU$3,290 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?
- Choose your dates: What you'd like to do in Gloucester and your favourite season will help you decide when to get away.
- 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.
- 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.
- Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.