Gloucester Vacations from ¥412,514

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The Latest Gloucester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common
Boston Harbor Hotel
Eurostars The Boxer
The Lenox Hotel Boston
The Langham, Boston

Where to stay in Gloucester

Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester

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 ¥28,526 per night from Jun 3 to Jun 4
¥28,526
¥31,863 total
Jun 3 - Jun 4
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Beautiful inn with a lovely view. Rooms were exceptionally clean and had a full size balcony to be enjoyed. Plenty of parking and pleasant staff. Conveniently located off the highway and near the event I attended. My one major complaint was no mention from the staff or signage that the buffet breakfast ..."

Reviewed on May 24, 2026

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is ¥55,903 per night from Jun 7 to Jun 8
¥55,903
¥62,444 total
Jun 7 - Jun 8
includes taxes & fees
9.6/10 Exceptional! (966 reviews)
"From the front desk to the dinning room everything was great. Everyone was helpful and what an amazing hotel"

Reviewed on May 23, 2026

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 ¥25,683 per night from Jun 4 to Jun 5
¥25,683
¥32,601 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (830 reviews)
"Amazing property wished I could have stayed a week, view spectacular and the amenities were amazing! This is place is worth a visit!!!"

Reviewed on May 28, 2026

Ocean House Hotel at Bass Rocks
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.