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 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,756 reviews)
The room met our needs. It was clean and the breakfast was nice.
Reviewed on Jun 15, 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 9 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
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
The price is CA $172 per night from Jul 14 to Jul 15
CA $172
CA $212 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (2,506 reviews)
"Our ac didn’t work. It was over 90 degrees."
Reviewed on Jun 15, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $130 per night from Jun 18 to Jun 19
CA $130
CA $187 total
Jun 18 - Jun 19
includes taxes & fees
9/10 Wonderful! (3,530 reviews)
"We had a 2 bedroom unit. There is no ceiling lights in the bedrooms. The 2 twin beds room had only a table lamp that was not very bright. The master king bedroom had 2 table lamps that did not provide adequate lighting. Many times, I went into another room with ceiling lights to be able to see ..."
Reviewed on Jun 15, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
The price is CA $124 per night from Jul 12 to Jul 13
CA $124
CA $174 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,780 reviews)
"We only stayed for two nights, arriving at about 2:00 AM. The staff was great, the continental breakfast is a little bit of a zoo. Plenty of food constantly replenished, but, lots of people standing in a long slow moving line and hard to find a table to eat at. My only complaint/warning is that when ..."
Reviewed on Jun 15, 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.
