Downtown Gloucester Holidays from AU$2,173
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Top Holiday Package Deals in Downtown Gloucester
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
AU$3,030
per person
19 Nov - 24 Nov
found 5 hours ago
Return flight included
Melbourne (MEL) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This hotel is one of, if not the, nicest hotels I have ever stayed at around the world. The level of service is second to none, and hotel itself, physically, is incredibly elegant. Being situated on Boston Harbor puts this hotel over the top and into a class of its own.
Reviewed on 16 Oct 2026
Our guide on where to stay in Downtown Gloucester
Find the best Downtown Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Gloucester
East Gloucester
2 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.
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.
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.
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.
Our pick of the best Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
AU$314
16 Nov - 17 Nov
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Great location, cool vibe, comfortable facilities."
Reviewed on 16 Oct 2026
The Highliner Hotel
108 Main St Gloucester MA
AU$482
12 Nov - 13 Nov
includes taxes & fees
8.8/10 Excellent! (23 reviews)
"Loved our room. Very elegant and immaculate. Absolutely excellent location. Celebrated our 24th anniversary in style. Parking is a little walk. Would recommend dropping off one person and luggage then go park."
Reviewed on 12 Oct 2026
Harborview Inn
71 Western Avenue Gloucester MA
AU$304
8 Nov - 9 Nov
includes taxes & fees
9.6/10 Exceptional! (339 reviews)
"What a great place! Great location facing Gloucester Harbor. Lovely charming house. Easy parking. Wonderful clean room with comfy bed and all amenities. Welcoming hosts. I’d gladly come back. Really good value too."
Reviewed on 14 Oct 2026
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 Downtown Gloucester attractions
Maritime Gloucester
9.4/10 (63 reviews)
You can spend an afternoon studying the exhibits at Maritime Gloucester during your trip to Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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.
Fishermen's Memorial Monument
9.6/10 (18 reviews)
Learn about the local history of Gloucester when you spend time at Fishermen's Memorial Monument. Wander through the beautiful beaches and seaside in this family-friendly area.
Pavilion Beach
8.0/10 (9 reviews)
Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester?
Capt Bill & Sons Whale Watch
8.2/10 (12 reviews)
You can learn about the history of Gloucester with a stop at Capt Bill & Sons Whale Watch. Wander the seaside and beautiful beaches in the area.
Gloucester Unitarian Universalist Church
After visiting Gloucester Unitarian Universalist Church, make a plan to see the other sights and activities in Gloucester.
Sargent House Museum
6.0/10 (1 review)
You can spend time exploring the galleries in Sargent House Museum during your travels in Gloucester. Wander the seaside and beautiful beaches in the area.
Schooner Adventure
You can spend time studying the exhibits at Schooner Adventure during your travels in Gloucester. Wander the seaside and beautiful beaches in the area.
Activities
Cape Ann Harbor: Self-Guided Driving Audio Tour
AU$24
per traveller
100% of travellers recommend
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
AU$70
per adult
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
AU$24
per traveller
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.