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.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Price was CA $1,325, price is now CA $1,052 per person
CA $1,052
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,005 reviews)
Hot tub and vending machines have been removed. Dinner menu is extremely minimal. Staff was friendly and room was clean.
Reviewed on May 1, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,935, price is now CA $1,447 per person
CA $1,447
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
The resort staff amazing and the resort is beautiful! Rooms little outdated but clean!
Reviewed on May 18, 2026
Whispering Pines by Hotel O Whitestone VA
Price was CA $1,381, price is now CA $1,100 per person
CA $1,100
per person
Jul 4 - Jul 11
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
6.2/10 (154 reviews)
Not bad for a mid century motel. Room was small but I would call it european. Bathroom dated but clean. Needed a light bulb in shower, lampshade for table lamp, and smoke detector hooked up. When we checked in we had to air it out because of the sanitation smell but other than that I would stay again.
Reviewed on Oct 13, 2025
Kings Creek Plantation by TripForth
Price was CA $2,108, price is now CA $1,788 per person
CA $1,788
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (42 reviews)
This was probably the best property that I've stayed at, maybe ever. I had a family of 8 and the two apartments that we shared were perfect. I will be staying here again
Reviewed on Jul 13, 2025
King’s Creek Resort by Spinnaker
Price was CA $1,626, price is now CA $1,384 per person
CA $1,384
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (160 reviews)
The Kings Creek resort is beautiful, clean, comfortable, and conveniently close to the major area attractions. I would definitely stay there again for any trip to the Williamsburg VA area.
Reviewed on May 18, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (697 reviews)
"They didn't clean the room every day."
Reviewed on May 8, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jun 1 to Jun 2
CA $117
CA $150 total
Jun 1 - Jun 2
includes taxes & fees
8.8/10 Excellent! (2,416 reviews)
"The gate to the entrance was still open which seemed to result in many cars/people enter for what appeared to be a party woth 70-100 people and cars zipping around property. This went on for quite some time. I witnessed cars speeding around the parking area resulting in two vehicle hitting each other. ..."
Reviewed on May 18, 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 Jun 2 to Jun 3
CA $127
CA $184 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (3,485 reviews)
"We had a great time Everyone was very friendly and a lot to do on the property. They had a great assortment of pools to go into, miniature golf, tennis etc.. and the property was very nice to walk around and relax. The Restaraunt had great meals with great prices (especially for breakfast). We were ..."
Reviewed on May 19, 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.
