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.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Price was CA $11,050, price is now CA $7,442 per person
CA $7,442
per person
Aug 8 - Aug 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended.
Tim Lawler
Reviewed on Oct 8, 2025
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.
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
The price is CA $600 per night from Jul 27 to Jul 28
CA $600
CA $670 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (977 reviews)
"Wonderful hotel next to the sea. The property is conveniently located to the beach, restaurants, and stores. The room was spacious and comfortable. We enjoyed the L'Occitane bath products! Bed was comfortable. Enjoyed our time and recommend staying here."
Reviewed on Jul 3, 2026
The Highliner Hotel
108 Main St Gloucester MA
The price is CA $218 per night from Jul 19 to Jul 20
CA $218
CA $466 total
Jul 19 - Jul 20
includes taxes & fees
7.8/10 Good! (10 reviews)
"Very, very small. No place to put your “things”"
Reviewed on Jul 6, 2026
Harborview Inn
71 Western Avenue Gloucester MA
The price is CA $354 per night from Jul 20 to Jul 21
CA $354
CA $395 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (328 reviews)
"Great location across the street from the harbor. Proprietor (John) is very friendly and helpful. Highly recommend staying there. We have friends who live in the area (we don't) and we will definitely return to the Harborview on future visits."
Reviewed on Jul 6, 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
Things to do
Cape Ann Harbor: Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
CA $24
per traveller
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $64
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.