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.
King’s Creek Resort by Spinnaker
Price was CA $1,030, price is now CA $880 per person
CA $880
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (191 reviews)
Very clean and friendly for the most part except you were rushed by housekeeping to check out because they were busy. Overall a pleasant stay.
Reviewed on Jun 26, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,275, price is now CA $1,051 per person
CA $1,051
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
Loved the location. Bearing able to walk to everything. Staff was friendly and helpful. The rooms were very clean. The breakfast wasn’t much and the staff in there wasn’t as good as the rest of the hotel. The hotel overall just needs some updates and upkeep. Starting to look run down, but so was the visitor center.
Reviewed on Jun 27, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,360, price is now CA $1,150 per person
CA $1,150
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,019 reviews)
Waterviews, Marina/Beach, Pools, and the nightly visits of deer/bunnies.
Reviewed on Jun 26, 2026
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Price was CA $1,051, price is now CA $890 per person
CA $890
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,006 reviews)
We routinely stay at this specific hotel when we visit Williamsburg. The staff are very friendly, the rooms are clean and it’s a quiet hotel even when it’s full. It is also at a very convenient location for Busch Gardens and the Outlet mall. The only thing that I ca. mention is that the breakfast is an additional charge and is essentially the same breakfast that is free elsewhere. That’s a drawback. We will be regular customers due to the staff and the upkeep of the hotel!
Reviewed on Jun 26, 2026
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort
Price was CA $1,164, price is now CA $1,013 per person
CA $1,013
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (454 reviews)
Absolutely pleasantly surprised by how great the property, room, and staff was. Front desk was incredibly helpful, our room was very spacious and comfortable. Outdoor area was great for relaxing and comfortable.
Location couldn’t have been better. 1 mile to both downtown Williamsburg and to the nearest grocery store.
Would recommend to families, our 10 + 7YO were very impressed
Reviewed on Jun 22, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $148 per night from Jul 12 to Jul 13
CA $148
CA $164 total
Jul 12 - Jul 13
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 $175 per night from Jul 12 to Jul 13
CA $175
CA $215 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (2,536 reviews)
"The property and room are OK. The room was nice but noisy due to it being a bottom unit and a lot of road noise. The worst thing was that during our stay our car was broken into as individuals were going through cars, trying to unlock them, and then taking items. We were woken up at 12:45 AM by police ..."
Reviewed on Jun 27, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 12 to Jul 13
CA $132
CA $190 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (3,517 reviews)
"Enjoyed the rooms, pool, and location. Only issue was the heavy selling by the concierge desk for a time share, and the lack of check in staff available."
Reviewed on Jun 27, 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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