Gloucester Vacations from ￥225,455

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The Latest Gloucester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Beverly

The Beverly

3 out of 5
per person
Sep 12 - Sep 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Only complaint with 3 guests booked there was only one wash cloth provided one roll of toilet paper and one blanket for pull out bed no sheets other than that it was a good convenient place to stay

Reviewed on Aug 4, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
Sep 12 - Sep 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8/10 Very Good! (569 reviews)
Washer/Dryer did not work properly. Despite 2 calls and 1 email to customer service, the issue was not resolved. The washer didn’t rinse clothing out and they remained sopping wet. They required extensive drying time as a result ( over 4 hours). This was extremely inconvenient.

Reviewed on Aug 2, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Sep 12 - Sep 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,066 reviews)
Room was very cold thankful for staff to bring us more blankets. Room next to us was very noisy. Then in the am my shower was cold had it all the way to hot and it was like warm at best. Disappointing

Reviewed on Aug 2, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Sep 24 - Sep 29
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,013 reviews)
Beautiful hotel located right in the heart of the city! Nice big room with a big bathroom. Located near all the shopping and great restaurants. Also very close to the T station and very safe!

Reviewed on Jul 28, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
per person
Sep 24 - Sep 29
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,003 reviews)
Wonderful hotel, among the best I've stayed at worldwide. Excellent hotel restaurants and thoughtfully designed, comfortable rooms. Superbly sited for exploring Cambridge/Harvard and Boston in general. The only flaw is the conspicuous lack of a food safe mini fridge for leftovers and/or beer. Minibar only, in the year of our lord 2025? A comparatively minor quibble; I hope to return.

Reviewed on Aug 3, 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

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is ￥23,746 per night from Aug 11 to Aug 12
￥23,746
￥26,524 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Beautiful, hospitable staff and cute and quaint rooms. Wish the breakfast/dining area had been open but otherwise was fantastic!"

Reviewed on Aug 3, 2025

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is ￥70,015 per night from Sep 3 to Sep 4
￥70,015
￥78,207 total
Sep 3 - Sep 4
includes taxes & fees
9.6/10 Exceptional! (866 reviews)
"This is a beautiful property and friendly staff. Food was excellent. Rooftop pool deck was amazing, although, a little crazy at times."

Reviewed on Aug 1, 2025

Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is ￥42,205 per night from Sep 1 to Sep 2
￥42,205
￥50,588 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (722 reviews)
"Gorgeous views."

Reviewed on Jul 22, 2025

Ocean House Hotel at Bass Rocks
See all 1,777 properties in Gloucester
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 which includes heritage elements, general coastal views and a sunset

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.

Hammond Castle
Fishermen\'s Memorial Monument showing a statue or sculpture

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.

Fishermen's Memorial Monument

What to do in Gloucester

Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

￥3,175
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
Mysteries & Murders of Salem Guided Night-Time Walking Tour

Mysteries and Murders of Salem Guided Night-Time Walking Tour

￥5,169
per adult
92% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
"Wicked History Unveiled: Salem's Most Enigmatic Witch Tour"

Salem Ghosts: Witches, Warlocks, & Hauntings

￥3,840
per adult
100% of travellers recommend
Salem Ghosts: Witches, Warlocks, & Hauntings
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from ￥225,455 on Expedia, you'll be thrilled with how little a vacation to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester vacation packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester vacation. With a well-organized schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester vacation on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
How to find the best Gloucester package deals?
Use Expedia's filters to find some great Gloucester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Gloucester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Gloucester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Gloucester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Gloucester?
If you're considering a spontaneous Gloucester getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Gloucester?

  1. Choose your dates: What you'd like to do in Gloucester and your favorite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you're up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the right Gloucester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.