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.
Vacation Village At Williamsburg
Price was CA $1,222, price is now CA $963 per person
CA $963
per person
Jul 18 - Jul 23
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (2,440 reviews)
They have gas grills and that is convenient but they do not supply grill tools and they don’t have a lighter for the grill. They kept running out of towels. We didn’t know they had hot plates in the rooms until we talked to other guests because we couldn’t understand why there were pots and pans and no stove top. The pullout couch only had a mattress pad there weren’t any sheets. It was a nice place over all
Reviewed on Jun 10, 2026
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,514, price is now CA $1,113 per person
CA $1,113
per person
Jul 18 - Jul 23
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (820 reviews)
This hotel has absolutely massive rooms by today's standards and shares all amenities with the much more expensive Williamsburg Inn and Williamsburg lodge. The tradeoffs are that you will not have a front desk and the furniture and finishes are much older.
The reality, however, is that the tradeoffs are 100% worth it. The cost is half that of the Lodge and half to 1/4 of the cost of the Inn. You can still use the pool, spa, tennis courts, fitness facilities, concierge, ticket discounts, and everything else that comes with a stay at the fancier neighboring hotels. I would recommend the Griffin. No notes.
Reviewed on May 29, 2026
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Price was CA $1,283, price is now CA $993 per person
CA $993
per person
Jul 18 - Jul 23
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
Loved the suite layout. Very clean with friendly staff. Great place to stay!
Reviewed on Jun 8, 2026
Wedmore Place
Price was CA $1,480, price is now CA $1,167 per person
CA $1,167
per person
Jul 18 - Jul 23
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,003 reviews)
Beautiful hotel with European feel surrounded by nature and winery. Great breakfast!
Reviewed on May 27, 2026
Club Wyndham Governor’s Green
Price was CA $1,534, price is now CA $1,211 per person
CA $1,211
per person
Jul 18 - Jul 23
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (251 reviews)
Wonderful experience once again. Indoor pool was ice cold due to a broken thermostat. Hopefully it will be fixed when we return.
Reviewed on May 5, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $140 per night from Jul 9 to Jul 10
CA $140
CA $155 total
Jul 9 - Jul 10
includes taxes & fees
7.2/10 Good! (707 reviews)
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."
Reviewed on Jun 9, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
The price is CA $168 per night from Jun 16 to Jun 17
CA $168
CA $207 total
Jun 16 - Jun 17
includes taxes & fees
8.8/10 Excellent! (2,481 reviews)
"They have gas grills and that is convenient but they do not supply grill tools and they don’t have a lighter for the grill. They kept running out of towels. We didn’t know they had hot plates in the rooms until we talked to other guests because we couldn’t understand why there were pots and pans ..."
Reviewed on Jun 10, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $129 per night from Jun 14 to Jun 15
CA $129
CA $187 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (3,503 reviews)
"Unit was clean, spacious, and easily accessible. We’ve stayed here multiple times now and would highly recommend."
Reviewed on Jun 10, 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.
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.
