Gloucester Vacations from ₩3,410,458
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The Latest Gloucester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Boston
Downtown Boston
₩3,410,458
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.6/10 Exceptional! (5,158 reviews)
Hotel was perfect location for my first real trip in Boston. Everything seemed at a walkable distance whether it’s food options, parks, subway access, or just fun city activities. Staff was amazing! Appreciate all the little details of individual toiletries, robes/slippers, and adequate amount of outlets. Would definitely recommend this hotel!
Reviewed on Aug 7, 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
3 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.
Downtown Gloucester
3 out of top 10 points of interest in this area
While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.
Annisquam
While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.
Rocky Neck
If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing.
Magnolia
Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.
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
₩252,148
₩328,826 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Room was clean and comfortable with a nice view. My only gripe was having no iron and board for ironing clothes before going out. We didn't have breakfast so i really don't know how that would have gone. I liked the location being close to downtown. Staff was awesome."
Reviewed on Aug 5, 2026
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
₩594,257
₩663,785 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (996 reviews)
"Absolutely beautifully decorated, clean and we felt like we were on a resort especially with the pool on the roof top with a bar and music."
Reviewed on Aug 6, 2026
Ocean House Hotel at Bass Rocks
107 Atlantic Rd Gloucester MA
₩404,445
₩486,723 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (854 reviews)
"Great views, clean, comfortable bed, modern furniture, balcony facing the ocean."
Reviewed on Jul 26, 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.
Stay near popular Gloucester attractions
Wingaersheek Beach
9.4/10 (83 reviews)
This pristine beach captivates with white sands, clear shallow waters, and dramatic rock formations. Visit at low tide to explore expansive sandbars and discover hidden tide pools teeming with marine life.
Good Harbor Beach
9.2/10 (191 reviews)
Stroll along Good Harbor Beach's pristine white sands, walking to Salt Island at low tide. Reserve summer parking in advance to enjoy this Atlantic gem with its gentle surf and family-friendly atmosphere.
Hammond Castle
9.4/10 (86 reviews)
Explore this 1920s medieval-style castle built by inventor John Hays Hammond Jr. on Massachusetts' coast. Wander through grand halls filled with Roman and Renaissance artifacts while enjoying dramatic ocean views.
Half Moon Beach
9.0/10 (45 reviews)
This crescent-shaped cove offers calm waters and golden sand within historic Stage Fort Park. Explore the rocky cliffs for picturesque views of Gloucester Harbor while enjoying the tranquil atmosphere.
Stage Fort Park
9.2/10 (71 reviews)
After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
Maritime Gloucester
9.4/10 (63 reviews)
Maritime Gloucester showcases the oldest operating marine railway in the US alongside interactive exhibits of local marine life. Explore the historic Dory Shop or sail the harbor aboard the traditional Schooner Ardelle.
Cape Ann Museum
9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area.
Capt Bill & Sons Whale Watch
8.2/10 (12 reviews)
Join marine experts on a 4-hour adventure to spot humpback, fin, and minke whales in their natural habitat. Naturalists from the Blue Ocean Society provide fascinating insights while you cruise the waters off Gloucester.
Frequently asked questions
How much does a Gloucester vacation package cost?
Offering great value package deals from ₩3,410,458 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?
- Choose your dates: What you'd like to do in Gloucester and your favorite season will help you decide when to get away.
- 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.
- 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.
- 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.
