Downtown Gloucester Vacations from ₩807,888
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The Latest Downtown Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
₩807,888
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
9/10 Wonderful! (2,798 reviews)
The rooms was clean, however… the shared bathroom wasn't maintained properly or as expected. Nice hotel and view tho!
Reviewed on Aug 18, 2026
Eurostars The Boxer
West End
₩1,021,896
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
8.8/10 Excellent! (1,549 reviews)
The house keeping staff was the best in all my last 25 years of traveling on Hotels and my cruises on various cruise lines.
Reviewed on Aug 18, 2026
Arcadian Hotel
Coolidge Corner
₩843,648
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
8.2/10 Very Good! (4,382 reviews)
Stayed one night & didn’t have any problems, check in was a bit long but other then that nothing to complain about! Very clean place would stay again.
Reviewed on Aug 18, 2026
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
1 out of top 10 points of interest in this area
If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing.
Annisquam
While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.
Magnolia
Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
₩463,947
₩518,229 total
Sep 17 - Sep 18
includes taxes & fees
The Highliner Hotel
108 Main St Gloucester MA
₩296,761
₩552,941 total
Aug 19 - Aug 20
includes taxes & fees
8.6/10 Excellent! (17 reviews)
"Really well appointed rooms. Accessible and helpful concierge. Convenient to restaurants and shops."
Reviewed on Aug 15, 2026
Harborview Inn
71 Western Avenue Gloucester MA
₩352,504
₩393,743 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (334 reviews)
"Love love love this place!!! John is so friendly and helpful, breakfast bar was perfect , the atmosphere of the room and breakfast area was so very relaxing. Can’t wait to go back again next year!!!"
Reviewed on Aug 15, 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
Cape Ann Museum
9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
Maritime Gloucester
9.4/10 (63 reviews)
You can spend an afternoon studying the exhibits at Maritime Gloucester during your travels in Gloucester. Wander 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?
Fishermen's Memorial Monument
9.6/10 (18 reviews)
Learn about the local history of Gloucester with a stop at Fishermen's Memorial Monument. Wander the beautiful beaches and seaside in this family-friendly area.
Capt Bill & Sons Whale Watch
8.2/10 (12 reviews)
You can learn about the history of Gloucester when you stop by 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.
Cape Ann Historical Museum
6.0/10 (1 review)
You can spend an afternoon exploring the galleries in Cape Ann Historical Museum during your trip to Gloucester. Wander the seaside and beautiful beaches in the area.
Sargent House Museum
6.0/10 (1 review)
You can spend time studying the exhibits at Sargent House Museum in Gloucester. Wander the seaside and beautiful beaches in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.