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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.


Turnpike Motel Richmond VA by Hotel O US 60
Midlothian
Price was CA $1,051, price is now CA $885 per person
CA $885
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.4/10 (94 reviews)
It was great for a quick overnight stay. Smoking room and clean was key for me. I will there were a couple of burn marks on things like people don't know how to use an ashtray. Other than that no problems. Also great customer service!
Reviewed on Mar 1, 2026

King’s Creek Resort by Spinnaker
Price was CA $1,435, price is now CA $1,226 per person
CA $1,226
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (175 reviews)
We had a small issue when we got to our first unit. Apparently housekeeping had reported the air conditioning wasn’t working, but we were still checked into the unit anyway and we were met by the maintenance tech when we were unpacking our car. We switched to a second unit which was perfect, except the phone in the unit didn’t work, so we had to call from ours cell phones, which wasn’t that big of a deal. The paper they gave us at check in with hours of the activity center (and on the QR code you scan in your unit) were incorrect, we walked in 10 min before 6 and the young lady told us, yeah we have been trying to communicate with them, but I’ve only been here 2 weeks.
All in all, this is the 2nd time I’ve stayed here and honestly haven’t had any true issues that won’t bring me back the next time I come to Williamsburg. Staff is super friendly, pools are clean, and the units are spacious. I will say, the pull out side beds need some kind of an update, my oldest wouldn’t even sleep on the bed part and just slept on the actual sofa for the few days we were there.
Reviewed on Jun 7, 2026

A house full of steel balls and games
Dumbarton
Price was CA $1,124, price is now CA $989 per person
CA $989
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.6/10 Exceptional! (113 reviews)
Had a great time with the pinball machines and game systems! Kids loved them too! And it was a great location right by the highway, but in a quiet neighborhood.
Reviewed on May 1, 2026
Gloucester Hotel Deals

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jun 17 to Jun 18
CA $169
CA $207 total
Jun 17 - Jun 18
includes taxes & fees
8.8/10 Excellent! (2,499 reviews)
"The resort was exactly as expected. The rooms were huge, the amenities matched the advertisements perfectly, and the location was super convenient to both Colonial Williamsburg and Busch Gardens. I would definitely stay here again!"
Reviewed on Jun 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 $130 per night from Jun 28 to Jun 29
CA $130
CA $187 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (3,511 reviews)
"My family and I have stayed at the Powhatan resort multiple times and we have always enjoyed our vacation there . The staff is excellent and the ladies that checked us in were terrific. We are already planning our family vacation for next year at the resort."
Reviewed on Jun 14, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
The price is CA $123 per night from Jul 15 to Jul 16
CA $123
CA $173 total
Jul 15 - Jul 16
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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