Gloucester Holidays from AU$2,880
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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.
The Latest Gloucester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Price was AU$4,190, price is now AU$3,562 per person
AU$3,562
per person
16 Nov - 21 Nov
found 4 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
8.8/10 Excellent! (1,071 reviews)
Great service from reception staff, and bustling cosy restaurant.
Reviewed on 13 Oct 2025
The Langham, Boston
Downtown Boston
Price was AU$5,496, price is now AU$4,719 per person
AU$4,719
per person
16 Nov - 21 Nov
found 4 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
Great location with easy walking to other districts.
Fabulous old hotel full of history but that has been tastefully renovated and upgraded.
Lovely hotel and our stay was made even better with the wonderful staff - a big thank you to Jenna on the concierge desk who gave us some fabulous restaurant recommendations and to Saleem on reception.
Reviewed on 14 Oct 2025
Hotel AKA Back Bay
Back Bay
Price was AU$3,413, price is now AU$2,995 per person
AU$2,995
per person
16 Nov - 21 Nov
found 4 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,150 reviews)
This area is expensive from what I’m told, and the price was definitely reflected when booking our stay. However, the hotel went above and beyond to provide us every service we could’ve ever asked for including yoga mats. And they did so in a timely and very easy manner. This hotel is also easy walking distance from most walking tours that you would complete in the Boston area and there was a couple of really nice breakfast spots located right around the corner. If the price wasn’t so high, I would absolutely stay here again, but would definitely look for something a little bit more affordable in the same neighborhood.
Reviewed on 15 Oct 2025
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
141 Essex Avenue, Gloucester, MA
The price is AU$276 per night from 2 Nov to 3 Nov
AU$276
2 Nov - 3 Nov
includes taxes & fees
8.2/10 Very Good! (1,018 reviews)
"Friendly staff."
Reviewed on 10 Oct 2025
Ocean House Hotel at Bass Rocks
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 4 Nov to 5 Nov
AU$254
4 Nov - 5 Nov
includes taxes & fees
9/10 Wonderful! (765 reviews)
"My absolute favorite was siting on our enormous porch overlooking the ocean!"
Reviewed on 8 Oct 2025
Sea Lion Motel and Cottages
138 Eastern Avenue, Gloucester, MA
The price is AU$297 per night from 20 Oct to 21 Oct
AU$297
20 Oct - 21 Oct
includes taxes & fees
9/10 Wonderful! (428 reviews)
"Great place"
Reviewed on 10 Oct 2025
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.
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.
Ravenswood Park
Explore the great outdoors at Ravenswood Park, a lovely green space in Gloucester. Wander the beautiful beaches and seaside in the area.
What to do in Gloucester
Bewitched Walking Tour of Salem
AU$53
per adult
98% of travellers recommend
Salem Uncovered: The Salem Witch Trials Tour
AU$55
per adult
80% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
AU$61
per adult
92% of travellers recommend
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Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
