Downtown Gloucester Vacations from ￥316,169
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The Latest Downtown Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
YOTEL Boston
Seaport District
Price was ￥365,288, price is now ￥316,169 per person
￥316,169
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
8.6/10 Excellent! (2,315 reviews)
Really happy with this stay. Clean rooms, friendly staff.
Reviewed on Jan 26, 2026
Boston Harbor Hotel
North End
Price was ￥532,994, price is now ￥406,222 per person
￥406,222
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026
The Whitney Hotel
Beacon Hill
Price was ￥386,017, price is now ￥318,940 per person
￥318,940
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Clean room that satisfied all needs. Great location in a quaint neighborhood
Reviewed on Jan 30, 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
3 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
9.6/10 Exceptional! (920 reviews)
The room was very clean, large as we had hoped. A great fireplace and ocean views made our brief get a way just perfect.
Reviewed on Jan 26, 2026
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is ￥14,469 per night from Feb 8 to Feb 9
￥14,469
￥16,161 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (2,389 reviews)
Clean room. Friendly staff. Would stay again!
Reviewed on Jan 31, 2026
Hawthorne Hotel
18 Washington Square W Salem MA
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,542 reviews)
I was happy with the room and staff
Reviewed on Jan 26, 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.
Discover the most popular places to visit in Downtown Gloucester
Fishermen's Memorial Monument
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.
Things to do
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
￥2,686
per traveler
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
￥7,904
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,904
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.