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.
King’s Creek Resort by Spinnaker
Price was CA $1,442, price is now CA $1,049 per person
CA $1,049
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.6/10 Excellent! (84 reviews)
Beautiful, clean, quiet, safe, friendly!
will come back!
Reviewed on Aug. 30, 2025
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,845, price is now CA $1,326 per person
CA $1,326
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (735 reviews)
The property is very large and offers many amenities, including spa and pools and golf. There are many restaurants in the different hotels that are part of the compound. The staff were very helpful and nice
Reviewed on Aug. 21, 2025
The Colonies at Williamsburg
Price was CA $1,762, price is now CA $1,331 per person
CA $1,331
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
9/10 Wonderful! (1,010 reviews)
The property was very clean, safe , and the people and staff were very friendly.
Reviewed on Aug. 30, 2025
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is CA $144 per night from Sep 4 to Sep 5
CA $144
CA $161 total
Sep 4 - Sep 5
includes taxes & fees
Hampton Inn Gloucester
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 11 to Sep 12
CA $186
CA $207 total
Sep 11 - Sep 12
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Sep 6 to Sep 7
CA $99
CA $152 total
Sep 6 - Sep 7
includes taxes & fees
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.