Gloucester Trips (flight + hotel)

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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.

Top hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is P9,191 per night from Aug 14 to Aug 15
P9,191
P10,266 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"Outlets were sketchy. Keurig coffee maker did nort work.VERY noisy. Listened to people"

Reviewed on Aug 8, 2025

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is P19,625 per night from Sep 9 to Sep 10
P19,625
P21,921 total
Sep 9 - Sep 10
includes taxes & fees
9.6/10 Exceptional! (871 reviews)
"Love the area for dining, shopping and relaxing."

Reviewed on Aug 8, 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 P14,133 per night from Sep 1 to Sep 2
P14,133
P17,120 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (727 reviews)
"Gorgeous views."

Reviewed on Jul 22, 2025

Ocean House Hotel at Bass Rocks
See all 1,796 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.

Popular places to visit

Wingaersheek Beach

Wingaersheek Beach

Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Wingaersheek Beach

What to do in Gloucester

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

P2,908
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

P2,908
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

P988
per traveler
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals 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.