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.
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
Wedmore Place
Price was CA $1,999, price is now CA $1,567 per person
CA $1,567
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,008 reviews)
Beautiful grounds. Wonderful staff. Very accommodating. Will be back!
Reviewed on Jun 27, 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 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
If you want to stay where it’s easy access to the visitors center for Colonial Williamsburg, The Woodlands is the perfect place. Very convenient access to everything in the surrounding areas. We have stayed multiple times and will stay again..
Reviewed on Jun 27, 2026
The Commonwealth
Downtown Richmond
Price was CA $1,630, price is now CA $1,416 per person
CA $1,416
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (1,377 reviews)
Location of hotel is excellent , across from the Capitol . Suite was very clean , beautiful bathroom .
i was not happy with the living area , walls were painted dark blue and there was no window . i had expected a view of the Capitol grounds but it was like living in a cage . I believe it false advertising because on line it showed a nice , comfortable , light room with a window .
I was told the hotel was full because of a convention and I could not change to another room .
Reviewed on Jun 25, 2026
King’s Creek Resort by Spinnaker
Price was CA $1,337, price is now CA $1,164 per person
CA $1,164
per person
Sep 9 - Sep 16
found 19 hours 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
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $153 per night from Jul 27 to Jul 28
CA $153
CA $171 total
Jul 27 - Jul 28
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 $180 per night from Jul 20 to Jul 21
CA $180
CA $220 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (2,531 reviews)
"We appreciated the space we had in the 2BR condo, and it was convenient to be able to cook some of our meals during our 3-night stay. It could certainly be updated—looked pretty dated. We also loved the pool during the weekday, but the Friday night was chaos with loud, unsupervised kids everywhere. ..."
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 $149 per night from Jul 7 to Jul 8
CA $149
CA $209 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (3,514 reviews)
"Pool was fun, room was clean"
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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