Downtown Gloucester Vacation Packages
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Top Holiday Package Deals in Downtown Gloucester
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $810
per person
Oct 21 - Oct 23
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Furnished Apartment Near Longwood
North Brookline
CA $1,697
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
6.8/10 (5 reviews)
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells.
Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.
Reviewed on Jul 6, 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
CA $451
CA $504 total
Sep 17 - Sep 18
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"Great rooftop pool and hot tub. Close access to a beach. Great food!"
Reviewed on Aug 22, 2026
The Highliner Hotel
108 Main St Gloucester MA
CA $214
CA $455 total
Sep 20 - Sep 21
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
CA $343
CA $383 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.
Things to do
Cape Ann Harbor: Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $71
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.