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 $1,310, price is now CA $1,061 per person
CA $1,061
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
Nice room good location.
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 9 hours 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
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 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,006 reviews)
My husband and I had a relaxing long weekend. Our room and hotel was clean. Housekeeping came in one day to tidy up and everything was perfect when we returned. They were very respectful of our room. I have to mention the bartenders! Carrie and Ramona were fabulous! Their drinks were perfect and they kept us laughing. These ladies made our trip!
Reviewed on Jun 23, 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 13 hours 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
The Commonwealth
Downtown Richmond
Price was CA $2,075, price is now CA $1,742 per person
CA $1,742
per person
Aug 7 - Aug 14
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
Gloucester Hotel Deals
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 23 to Jul 24
CA $194
CA $236 total
Jul 23 - Jul 24
includes taxes & fees
8.8/10 Excellent! (2,540 reviews)
"3 stars max"
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 $131 per night from Jul 15 to Jul 16
CA $131
CA $190 total
Jul 15 - Jul 16
includes taxes & fees
9/10 Wonderful! (3,518 reviews)
"Great place very big and beautiful. Great staff!"
Reviewed on Jun 25, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 19 to Jul 20
CA $122
CA $172 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (1,779 reviews)
"Nice room good location."
Reviewed on Jun 25, 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.
