Gloucester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,429, price is now CA $1,136 per person
CA $1,136
per person
Aug 10 - Aug 17
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
The Commonwealth
Downtown Richmond
Price was CA $1,896, price is now CA $1,485 per person
CA $1,485
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
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)
The room was beautiful, the setting in the winery next to woods was gorgeous, and the breakfast was delicious. Exceeded expectations for a mom traveling with two kids!
Reviewed on Jun 25, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,891, price is now CA $1,541 per person
CA $1,541
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,885, price is now CA $1,542 per person
CA $1,542
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.2/10 Very good! (1,000 reviews)
Although our stay was pleasant, we were disappointed to learn upon checking in at 5 PM that the room type we had booked several months in advance (a king suite) was no longer available.
Reviewed on Jun 25, 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 $194 per night from Jul 22 to Jul 23
CA $194
CA $236 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (2,528 reviews)
"Nice place! I would definitely come back again and refer it to others"
Reviewed on Jun 26, 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! (3,512 reviews)
"Very clean and spacious!"
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.
Stay near popular Gloucester attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
