Gloucester Vacations from ￥412,514
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common
Bay Village
Price was ￥532,158, price is now ￥412,514 per person
￥412,514
per person
Aug 5 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.4/10 Very Good! (1,463 reviews)
Rooms are not big but for me traveling solo and going out mostly it was great.
Reviewed on May 31, 2026
Boston Harbor Hotel
North End
Price was ￥793,998, price is now ￥506,479 per person
￥506,479
per person
Aug 5 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again
Reviewed on May 25, 2026
Eurostars The Boxer
West End
Price was ￥528,048, price is now ￥429,574 per person
￥429,574
per person
Aug 5 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.8/10 Excellent! (1,496 reviews)
Front desk staff was very friendly and accommodating
Reviewed on May 31, 2026
The Lenox Hotel Boston
Back Bay
Price was ￥557,723, price is now ￥465,320 per person
￥465,320
per person
Aug 5 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.6/10 Exceptional! (1,548 reviews)
The location is great, very close to all the nice shops on Exeter street, just across from the Boston Public Library. The staff were excellent, very helpful and polite. Be aware the hotel is an older property and they have chosen to maintain the same esthetic, so it has that old school hotel vibe. Bed was super comfortable, A/C was very cold, liked the pillow, had bathrobes, ironing board and iron for guest use. Big bathroom with a tub.
Reviewed on Jun 1, 2026
Where to stay in Gloucester
Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about 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.
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 ￥28,526 per night from Jun 3 to Jun 4
￥28,526
￥31,863 total
Jun 3 - Jun 4
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Beautiful inn with a lovely view. Rooms were exceptionally clean and had a full size balcony to be enjoyed. Plenty of parking and pleasant staff. Conveniently located off the highway and near the event I attended. My one major complaint was no mention from the staff or signage that the buffet breakfast ..."
Reviewed on May 24, 2026
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
The price is ￥55,903 per night from Jun 7 to Jun 8
￥55,903
￥62,444 total
Jun 7 - Jun 8
includes taxes & fees
9.6/10 Exceptional! (966 reviews)
"From the front desk to the dinning room everything was great. Everyone was helpful and what an amazing hotel"
Reviewed on May 23, 2026
Ocean House Hotel at Bass Rocks
107 Atlantic Rd Gloucester MA
Fully refundableReserve now, pay when you stay
The price is ￥25,683 per night from Jun 4 to Jun 5
￥25,683
￥32,601 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (830 reviews)
"Amazing property wished I could have stayed a week, view spectacular and the amenities were amazing! This is place is worth a visit!!!"
Reviewed on May 28, 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 Gloucester
Hammond Castle
4.5/5(8 reviews)
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
￥5,492
per adult
98% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
￥3,369
per adult
84% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
