Gloucester Vacations from ￥318,974
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The Latest Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay
Back Bay
Price was ￥437,150, price is now ￥318,974 per person
￥318,974
per person
Oct 7 - Oct 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,116 reviews)
Unbeatable location in back bay with access to rest, shopping, and train (T) stops. Safe elevators and neighborhood and walkable throughout back bay and to downtown Boston. Facilities in such historical building were impeccable and the staff superb. In-house bar and eating facilities were a plus. Wish bathroom was more updated and that at least a luggage rack be available.
Reviewed on Aug 29, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥785,828, price is now ￥494,198 per person
￥494,198
per person
Oct 11 - Oct 17
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Highly recommend! Beautiful and amazing service! Felt like 4 seasons or ritz service!
Reviewed on Aug 30, 2025
Raffles Boston
Back Bay
Save 100% on your flight
Price was ￥613,523, price is now ￥401,610 per person
￥401,610
per person
Oct 7 - Oct 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.
Reviewed on Aug 28, 2025
The Whitney Hotel
Beacon Hill
Price was ￥577,994, price is now ￥420,398 per person
￥420,398
per person
Oct 7 - Oct 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (443 reviews)
Was a great looking hotel. Comfy beds. Updates decor. Strange that there was no cooler/fridge in the room though.
Reviewed on Aug 30, 2025
Find the Best Gloucester Vacation Packages
Gloucester Beach Vacation
The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester vacation. If you're eager to save on your trip to Gloucester, we'll let you in on a secret — choose one of our Gloucester packages. Grab one close to Pavilion Beach, only 0.32 kilometers from the city center and a must-do while here. Alternatively, select a package that puts you closer to Cressy Beach, another gorgeous coastline. Whichever you choose, you'll be left with extra dollars in your travel budget to have fun with.
Things You Should Know About Gloucester
- Drift off to sleep to the gentle sounds of the sea in one of our Gloucester beach hotels. Nothing beats staying with walking distance of the ocean.
- Private vacation homes are another top choice for people planning a vacation in Gloucester. Some great examples are Castle Manor Inn and The Hotel at Cape Ann Marina.
- Roughly 29,800 people reside in Gloucester. If you want some tips about things to see and do here, why not start a conversation with some of the friendly locals? Our Gloucester things to do page is also a handy source of information.
- Don't head home without exploring Cape Ann, Capt Bill & Sons Whale Watch and Dogtown. With the cash you save through our Gloucester vacation deals, you can see more impressive attractions like these.
Gloucester Hotel Deals
Castle Manor Inn
141 Essex Avenue, Gloucester, MA
The price is ￥23,690 per night from Sep 1 to Sep 2
￥23,690
￥26,462 total
Sep 1 - Sep 2
includes taxes & fees
Ocean House Hotel at Bass Rocks
107 Atlantic Rd, Gloucester, MA
The price is ￥28,211 per night from Sep 4 to Sep 5
￥28,211
￥34,949 total
Sep 4 - Sep 5
includes taxes & fees
The Hotel at Cape Ann Marina
75 Essex Avenue, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is ￥30,881 per night from Sep 16 to Sep 17
￥30,881
￥34,494 total
Sep 16 - Sep 17
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.
Discover the most popular places to visit in Gloucester
Hammond Castle
You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.
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.
What to do in Gloucester
Massachusetts Highlights: Freedom Trail, Salem & More Tour
￥7,361
per adult
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
￥2,511
per traveler
80% of travellers recommend
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,361
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.