Gloucester Vacations from ￥67,886

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The Latest Gloucester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was ￥156,918, price is now ￥67,886 per person
￥67,886
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥266,370, price is now ￥142,074 per person
￥142,074
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug 26, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥183,960, price is now ￥108,174 per person
￥108,174
per person
Nov 20 - Nov 23
found 23 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug 24, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was ￥160,623, price is now ￥107,556 per person
￥107,556
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.2/10 Wonderful! (1,010 reviews)
Increased room daily charges at the time of checkout significantly

Reviewed on Aug 24, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was ￥176,656, price is now ￥118,544 per person
￥118,544
per person
Nov 20 - Nov 23
found 23 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Well appointed property, close to transit, downtown and highways. We had a lovely stay and look forward to returning soon.

Reviewed on Aug 25, 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 ￥23,754 per night from Sep 3 to Sep 4
￥23,754
￥26,533 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"The stay was amazing! We loved the area and the location was beautiful. John was great and attentive. 1000% recommend!"

Reviewed on Aug 23, 2025

Castle Manor Inn
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
The price is ￥30,965 per night from Sep 21 to Sep 22
￥30,965
￥34,588 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (725 reviews)
Lovely Getaway
"The staff was great, our room was lovely. Had dinner at Mile Marker 1, and it was delicious with a great view."

Reviewed on Aug 15, 2025

The Hotel at Cape Ann Marina
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is ￥25,509 per night from Sep 1 to Sep 2
￥25,509
￥28,493 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (412 reviews)
"Room was very clean, the shower was hot with water pressure and bed was comfortable. Win, win, win!"

Reviewed on Aug 22, 2025

Sea Lion Motel and Cottages
See all 1,764 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

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.

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

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

￥7,361
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

￥2,511
per traveler
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

￥7,361
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from ￥67,886 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.