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 1 day 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
Kingsmill Resort
Kingsmill
Price was CA $1,581, price is now CA $1,291 per person
CA $1,291
per person
Aug 22 - Aug 27
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,019 reviews)
Enjoyed the stay immensely. Food was great. Great river views.
Reviewed on Jun 21, 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 1 day 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 29 to Jun 30
CA $147
CA $164 total
Jun 29 - Jun 30
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 $179 per night from Jul 6 to Jul 7
CA $179
CA $220 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,521 reviews)
"Family friendly. No early check in long wait after noted check in time on website."
Reviewed on Jun 22, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 21 to Jul 22
CA $131
CA $189 total
Jul 21 - Jul 22
includes taxes & fees
9/10 Wonderful! (3,503 reviews)
"The pools and pool area was fantastic!! Check in is at 4:00 so we checked in then but had a two hour wait until our rooms were ready at 6:00. The wait was too long especially with a young child. We did get a drink at the restaurant and we played at the playground. But it was still too long a ..."
Reviewed on Jun 22, 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.
