Gloucester Vacation Packages
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Your Gloucester Vacation
From its coastal scenery to its rich history and beyond, there's loads to like about Gloucester. Discover the wonders of this captivating city with a Gloucester vacation package that's made for you. Eager to do a bit of sightseeing? A trip to Gloucester isn't complete without checking out Middle Peninsula State Park, Gloucester Museum of History and other major attractions. Your Gloucester vacation is clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
Top Gloucester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games
Dumbarton
Price was CA $1,519, price is now CA $1,233 per person
CA $1,233
per person
Aug 24 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Richmond (RIC)
9.6/10 Exceptional! (113 reviews)
Had a great time with the pinball machines and game systems! Kids loved them too! And it was a great location right by the highway, but in a quiet neighborhood.
Reviewed on May 1, 2026
Hilton Richmond Downtown
Downtown Richmond
Price was CA $2,120, price is now CA $1,765 per person
CA $1,765
per person
Aug 24 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Richmond (RIC)
8.2/10 Very Good! (1,011 reviews)
Great staff! Great downtown location! Clean and quiet.
Reviewed on Jun 4, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $147 per night from Jun 28 to Jun 29
CA $147
CA $164 total
Jun 28 - Jun 29
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"
Reviewed on Jun 20, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 5 to Jul 6
CA $174
CA $214 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,509 reviews)
"We enjoyed this property so much we tried to extend our stay but they were booked! We'll be back."
Reviewed on Jun 20, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jun 28 to Jun 29
CA $148
CA $208 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (3,499 reviews)
"Great stay"
Reviewed on Jun 20, 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.
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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.
