Downtown Gloucester Vacations from ￥344,714
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The Latest Downtown Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston
South End
Price was ￥440,940, price is now ￥344,714 per person
￥344,714
per person
Aug 6 - Aug 10
found 8 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Boston Harbor Hotel
North End
Price was ￥751,472, price is now ￥630,556 per person
￥630,556
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
Mandarin Oriental, Boston
Back Bay
Price was ￥557,594, price is now ￥476,694 per person
￥476,694
per person
Aug 6 - Aug 10
just found
Roundtrip non-stop flight included
Osaka (OSA) to Boston (BOS)
9.4/10 Exceptional! (432 reviews)
Terrible experience. Family of five with three youngsters. Despite being loyal to the MO brand for years, this Boston property is by far one of the worst we have stayed at.
To start, there were blood stains on the room carpet. Two rooms on the same floor were confirmed by staff when the booking was made, yet they were not available at check-in. Room service trays sat outside of rooms for hours without being collected. The bathroom was outdated, and the air conditioning was noisy. Overall, the property looked more like a Holiday Inn than a Mandarin Oriental.
We will never come back.
Reviewed on Jun 30, 2026
Encore Boston Harbor
Price was ￥459,906, price is now ￥408,362 per person
￥408,362
per person
Aug 6 - Aug 10
found 7 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Boston (BOS)
9.6/10 Exceptional! (3,888 reviews)
The gardens are beautiful and the free water shuttle is nice.
I wish the hotel had an indoor pool and places to sit inside other than the slot machines!!!
Reviewed on Jul 5, 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.
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
The price is ￥65,377 per night from Jul 12 to Jul 13
￥65,377
￥73,026 total
Jul 12 - Jul 13
includes taxes & fees
9.6/10 Exceptional! (976 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 ￥24,795 per night from Jul 19 to Jul 20
￥24,795
￥52,926 total
Jul 19 - Jul 20
includes taxes & fees
7.8/10 Good! (9 reviews)
"The room was exactly like the picture. Overall it was a very good experience. There’s no interactions with staff because everything is done online from checking in, paying for parking, upgrades if you decide to add and right down to checking out. No waiting in line. Many cute shops and restaurants ..."
Reviewed on Jun 28, 2026
Harborview Inn
71 Western Avenue Gloucester MA
The price is ￥40,174 per night from Jul 6 to Jul 7
￥40,174
￥44,874 total
Jul 6 - Jul 7
includes taxes & fees
9.6/10 Exceptional! (326 reviews)
"This B&B is a delightful property in an excellent location. The Inn owner, John, was so helpful and friendly. It is a great location within walkable distance to many restaurants.short drive to many sights. I would definitely stay here again."
Reviewed on Jun 24, 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 Self-Guided Driving Tour in Gloucester and Rockport
￥2,718
per traveler
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
￥7,996
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,996
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.