East Gloucester Vacation Packages
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Top Holiday Package Deals in East Gloucester
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $755
per person
Oct 21 - Oct 23
found 1 day 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
Fairmont Copley Plaza, Boston
Back Bay
CA $1,579
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (1,325 reviews)
Beautiful hotel excellent location very helpful staff Highly recommend for your next trip to Boston
Reviewed on Aug 27, 2026
Where to stay in East Gloucester
Find the best East Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about East Gloucester
Downtown Gloucester
3 out of top 10 points of interest in this area
While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.
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.
Rocky Neck
1 out of top 10 points of interest in this area
While Rocky Neck might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rocky Neck Art Colony and Maritime Gloucester.
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.
East Gloucester Hotel Deals
Sea Lion Motel and Cottages
138 Eastern Avenue Gloucester MA
CA $240
CA $268 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (479 reviews)
"Staff was most helpful. Our room was near a busy road, so we heard cars at night. Very basic, but comfortable room. Bedding was excellent. Walk to Good Harbor is doable, but walk back up the hill could be tough if you have a lot to carry."
Reviewed on Aug 25, 2026
The Vista
22 Thatcher Rd. Gloucester MA
CA $314
CA $351 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (441 reviews)
"The staff are super duper friendly,"
Reviewed on Aug 28, 2026
Ocean House Hotel at Bass Rocks
107 Atlantic Rd Gloucester MA
Fully refundableReserve now, pay when you stay
CA $405
CA $486 total
Sep 1 - Sep 2
includes taxes & fees
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 East Gloucester attractions
Good Harbor Beach
9.2/10 (191 reviews)
Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.
Niles Beach
8.0/10 (8 reviews)
Why not spend a carefree afternoon at Niles Beach during your travels in Gloucester? Make some time to visit the shops while you're in the area.
Eastern Point Lighthouse
8.8/10 (38 reviews)
Learn about the local history of Gloucester with a stop at Eastern Point Lighthouse. Wander the beautiful beaches and seaside in this family-friendly area.
The Gorton Theatre
8.4/10 (6 reviews)
You can make plans for a show at The Gorton Theatre during your trip to Gloucester. Wander the beautiful beaches and seaside in this family-friendly 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.