
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.

Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA
Price was CA $1,236, price is now CA $1,084 per person
CA $1,084
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
7.6/10 Good! (46 reviews)
Breakfast was delicious and the staff was so friendly and helpful when my children asked for assistance! We will be back to visit!
Reviewed on Apr 15, 2026

Kingsmill Resort
Kingsmill
Price was CA $1,961, price is now CA $1,623 per person
CA $1,623
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
Fabulous resort - we stay there every chance we get!
Reviewed on Apr 13, 2026

Colonial Houses, an Official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,324, price is now CA $1,153 per person
CA $1,153
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (551 reviews)
What a treat to get to stay in a historic building in Colonial Williamsburg! Our room at the old tavern was very comfortable and we loved taking our morning cup of coffee out to the back porch and then walking through the still streets. In addition, the staff at the Williamsburg Inn went above and beyond for us during our stay. When we discovered that the rental car wouldn’t start in the morning, the check-in staff sprang into action. Our bags were tucked in a secure place and they drove us to make sure my daughter made it to her interview. Then, when the tow truck still hadn’t arrived two hours later, Adrian kindly drove over to our vehicle and with a little help from YouTube we were able to restart the car. Everyone on the staff was so kind and helpful! Thank you!
Reviewed on Apr 7, 2026

Holiday Inn Express Gloucester by IHG
Price was CA $1,314, price is now CA $1,183 per person
CA $1,183
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
7.2/10 Good! (682 reviews)
This was a typical Holiday Inn Express - clean, comfy, friendly and convenient. It was a great stop on our road trip. Comfy and quiet room, very clean. Breakfast had sufficient choices and the food was hot. I used the workout room, too, and it was small, but nice. We have come to trust the quality and cleanliness of Holiday Inn Express, and almost always book them when on trips.
Reviewed on Apr 7, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $167 per night from May 11 to May 12
CA $167
CA $186 total
May 11 - May 12
includes taxes & fees
7.2/10 Good! (688 reviews)
Perfect
Reviewed on Apr 10, 2026

Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 5 to May 6
CA $167
CA $186 total
May 5 - May 6
includes taxes & fees
9.2/10 Wonderful! (753 reviews)
Parking was sufficient.
Reviewed on Apr 11, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 19 to May 20
CA $127
CA $183 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (3,457 reviews)
I love this place! From the moment I drove up the driveway surrounded by manicured lawns and the Magnificent Powhatan mansion I was awed. The unit itself was just perfect. Two bedrooms two baths a full kitchen with utensils and a back deck overlooking a small pond. The weather cooperated so I was ...
Reviewed on Apr 20, 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.








