Gloucester Holidays

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Gloucester Beach Holiday

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester holiday. 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 kilometres from the city centre 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 holiday homes are another top choice for people planning a holiday 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 holiday 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 S$210 per night from 18 Aug to 19 Aug
S$210
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Incredibly friendly staff. The room was nice and clean. A+"

Reviewed on 6 Aug, 2025

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is S$494 per night from 9 Sept to 10 Sept
S$494
9 Sept - 10 Sept
includes taxes & fees
9.6/10 Exceptional! (871 reviews)
"Love the area for dining, shopping and relaxing."

Reviewed on 8 Aug, 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
Fully refundableReserve now, pay when you stay
The price is S$400 per night from 9 Sept to 10 Sept
S$400
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (723 reviews)
"Gorgeous views."

Reviewed on 22 Jul, 2025

Ocean House Hotel at Bass Rocks
See all 1,772 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.

What to do in Gloucester

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

S$64
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

S$64
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

S$22
per traveller
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 holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 holiday. With a well-organised 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 holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday 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 holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 favourite 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 accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.