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.
The Commonwealth
Downtown Richmond
Price was CA $845, price is now CA $612 per person
CA $612
per person
Sep 4 - Sep 7
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
The staff was exceptional, great hospitality! The room had several minor issues, shower door didn’t stay closed, vanity was missing a leg, power bank on one side of the bed didn’t work, a random ballon was on the ceiling(granted we didn’t notice it one of the staff did while trying to get the power bank to work) bar and restaurant was out of multiple items.
Reviewed on Jul 13, 2026
Quirk Hotel Richmond
Downtown Richmond
Price was CA $990, price is now CA $816 per person
CA $816
per person
Sep 4 - Sep 7
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,007 reviews)
The hotel was not what I expected. It was not in a great area of Richmond with no drugstore or coffeeshops (that we found) around the hotel..everything we wanted to see was a cab ride ($20) away.
The room was large but not any hooks in the bathroom except in the shower! And water went all over the floor while showering.
BUT we loved Richmond and will be back. Just not at the Quirk.
Reviewed on Jul 12, 2026
Graduate by Hilton Richmond
Downtown Richmond
Price was CA $766, price is now CA $631 per person
CA $631
per person
Sep 4 - Sep 7
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.4/10 Very good! (1,402 reviews)
bathroom would not work right and no one ever showed up to help I was told at front desk I coud have just called from room to report this but phone didnot have a cord attached to phone
Reviewed on Jul 13, 2026
Gloucester Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Aug 12 to Aug 13
CA $156
CA $193 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (2,611 reviews)
"The hotel was s"
Reviewed on Jul 12, 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 $108 per night from Jul 22 to Jul 23
CA $108
CA $156 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,824 reviews)
"This was a fabulous place to stay. It is an older hotel but very well run and the staff are was so accommodating and helpful! The only down side was no microwave in the room."
Reviewed on Jul 13, 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 19 to Jul 20
CA $131
CA $189 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (3,618 reviews)
"I think they need better flooring upstairs since it sounds like elephants walking over top when you have a bottom unit."
Reviewed on Jul 13, 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.
