Gloucester Vacations from ￥194,248
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The Latest Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Maverick Suites at 245 Newbury St
Back Bay
Price was ￥240,828, price is now ￥194,248 per person
￥194,248
per person
Nov 12 - Nov 17
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.2/10 Very Good! (141 reviews)
Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library
Reviewed on Oct 3, 2025
Iris Hotel Boston
Coolidge Corner South Side
Price was ￥272,435, price is now ￥215,502 per person
￥215,502
per person
Nov 12 - Nov 17
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (395 reviews)
This is a great hotel in a great location! Convenient to the green line and also walkable to a lot of things. We are a family of 5 and were happy they had a room to accommodate all of us that wasn’t outrageous. 2 queens and a pull out couch. Perfect! Bath products smell great and are high quality. Overnight valet parking but it’s unlimited in and out- which we didn’t do since we walked or took the train everywhere. And the staff who work here are welcoming, kind, and very helpful. This hotel is a gem! Highly recommend!
Reviewed on Oct 12, 2025
Ginkgo House on Harvard
Central Square
Price was ￥246,236, price is now ￥201,930 per person
￥201,930
per person
Nov 12 - Nov 17
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (66 reviews)
Everything was clean and staff was very hospitable
Reviewed on Oct 12, 2025
Hampton Inn Boston Seaport District
Seaport District
Price was ￥255,640, price is now ￥210,464 per person
￥210,464
per person
Nov 12 - Nov 17
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (2,541 reviews)
Staff was very friendly! Every staff member that I walked by or around greeted me.
Reviewed on Oct 7, 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 ￥24,357 per night from Nov 2 to Nov 3
￥24,357
￥27,206 total
Nov 2 - Nov 3
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Y"
Reviewed on Oct 6, 2025
Ocean House Hotel at Bass Rocks
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is ￥19,610 per night from Nov 3 to Nov 4
￥19,610
￥25,440 total
Nov 3 - Nov 4
includes taxes & fees
9/10 Wonderful! (763 reviews)
"The Ocean House hotel was the exact boutique New England experience we were searching for. The hotel does show its age, however this did not take away from the stay."
Reviewed on Oct 6, 2025
Sea Lion Motel and Cottages
138 Eastern Avenue, Gloucester, MA
The price is ￥26,156 per night from Oct 13 to Oct 14
￥26,156
￥29,216 total
Oct 13 - Oct 14
includes taxes & fees
9/10 Wonderful! (427 reviews)
"Clean room. Great breakfast, view of the ocean and chairs and a small deck out back of the room. Very relaxing and enjoyable!"
Reviewed on Oct 6, 2025
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
Bewitched Walking Tour of Salem
￥5,127
per adult
98% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
￥5,273
per adult
92% of travellers recommend
Salem Ghosts: Witches, Warlocks, & Hauntings
￥4,687
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
