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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $956, price is now CA $805 per person
CA $805
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,756 reviews)
Property was awesome. Lots to see and do. Room was nice and comfortable. The only issue I had was the breakfast was a bit meh, but it was free so kind of hard to complain.
Reviewed on Jun 16, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,382, price is now CA $1,146 per person
CA $1,146
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,009 reviews)
Great pool area though the lazy river wasn't functioning.
Reviewed on Jun 13, 2026
Turnpike Motel Richmond VA by Hotel O US 60
Midlothian
Price was CA $1,052, price is now CA $886 per person
CA $886
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.4/10 (94 reviews)
It was great for a quick overnight stay. Smoking room and clean was key for me. I will there were a couple of burn marks on things like people don't know how to use an ashtray. Other than that no problems. Also great customer service!
Reviewed on Mar 1, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $140 per night from Jul 16 to Jul 17
CA $140
CA $156 total
Jul 16 - Jul 17
includes taxes & fees
7.2/10 Good! (707 reviews)
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."
Reviewed on Jun 9, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
The price is CA $186 per night from Jun 30 to Jul 1
CA $186
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (2,507 reviews)
"Great place to stay with family"
Reviewed on Jun 16, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $130 per night from Jun 22 to Jun 23
CA $130
CA $187 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (3,531 reviews)
"Big spacious rooms great staff and in a great location to do things outside of the club if need be"
Reviewed on Jun 16, 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.
