Gloucester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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$253 per night from 9 Nov to 10 Nov
S$253
9 Nov - 10 Nov
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Staff was very nice and helpful with late check-in. Room was very clean, big comfortable bed, and lovely view from the balcony. Only complaint is that the walls are very thin and we could hear the people next door very loudly, and could hear outside very loud as well. Overall positive experience ...

Reviewed on 3 Nov, 2025

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 S$219 per night from 9 Nov to 10 Nov
S$219
9 Nov - 10 Nov
includes taxes & fees
9/10 Wonderful! (782 reviews)
Clean comfortable room. Beautiful view.

Reviewed on 1 Nov, 2025

Ocean House Hotel at Bass Rocks
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
9.6/10 Exceptional! (893 reviews)
Excellent facility we really enjoyed our stay. It’s very close to a lot of amenities.

Reviewed on 24 Oct, 2025

Beauport Hotel 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

* 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.