Gloucester Vacations from NT$31,890

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The Latest Gloucester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Falmouth Tides

Falmouth Tides

2.5 out of 5
Falmouth Heights
Save 100% on your flight
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
9.2/10 Wonderful! (590 reviews)
Staff was amazing hidden gem

Reviewed on 2025/7/26

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Sep 17 - Sep 21
found 2 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on 2025/7/23

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 17 - Sep 21
found 2 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
The property is conveniently located to the major roads and is in walkable distance to the main historical landmarks.

Reviewed on 2025/7/24

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
Sep 17 - Sep 21
found 2 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Safe location. Clubs across the street for a night out. Fairly close to tourist things. Rooms are clean but on the smaller side.

Reviewed on 2025/7/24

The Boxer

The Boxer

4 out of 5
West End
per person
Sep 17 - Sep 21
found 2 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
8.6/10 Excellent! (1,236 reviews)
This hotel is super cute. Our room was pretty tiny but the proximity to the TD Garden is what makes this the real winner. If you are super sensitive to noise the water running through the pipes is quite loud. It never woke me up but it was annoying when we were relaxing in our room. As far as noise goes, we never heard anyone in the hallway.

Reviewed on 2025/7/22

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 NT$4,726 per night from Jul 28 to Jul 29
NT$4,726
NT$5,279 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Quaint little inn, very clean and comfortable, just what we needed."

Reviewed on 2025/7/25

Castle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is NT$10,957 per night from Aug 25 to Aug 26
NT$10,957
NT$12,927 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (721 reviews)
"Gorgeous views."

Reviewed on 2025/7/22

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is NT$9,540 per night from Aug 25 to Aug 26
NT$9,540
NT$10,656 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (425 reviews)
"Clean, quiet, beautiful place to stay.great service. Good food."

Reviewed on 2025/7/3

Atlantis Oceanfront Inn
See all 1,778 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

Good Harbor Beach which includes a sunset and a coastal town

Good Harbor Beach

4.5/5(18 reviews)

If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Good Harbor Beach
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
Half Moon Beach which includes a beach, general coastal views and a sunset

Half Moon Beach

If a restful vacation is part of your travel plans, Half Moon Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

Half Moon Beach

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from NT$31,890 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.