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.
A house full of steel balls and games
Dumbarton
Price was CA $959, price is now CA $745 per person
CA $745
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Richmond (RIC)
9.6/10 Exceptional! (112 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
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,809, price is now CA $1,365 per person
CA $1,365
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Richmond (RIC)
8.2/10 Very Good! (1,004 reviews)
Breakfast was delicious, the rooms were clean, the beds were extremely comfortable, the we really enjoyed the restaurant for a light meal
Reviewed on May 17, 2026
The Commonwealth
Downtown Richmond
Price was CA $1,421, price is now CA $1,137 per person
CA $1,137
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Richmond (RIC)
8.8/10 Excellent! (1,354 reviews)
The rooms are very clean and spacious, the staff very friendly and helpful.
Good location
Reviewed on May 26, 2026
Graduate by Hilton Richmond
Downtown Richmond
Price was CA $1,304, price is now CA $1,093 per person
CA $1,093
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Richmond (RIC)
8.4/10 Very Good! (1,371 reviews)
A wonderful hotel and pleasant staff!
Reviewed on May 31, 2026
Omni Richmond Hotel
Downtown Richmond
Price was CA $1,750, price is now CA $1,468 per person
CA $1,468
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Richmond (RIC)
9/10 Wonderful! (1,432 reviews)
It was very conveniently located and beautifully appointed. Helpful staff.
Reviewed on May 30, 2026
Gloucester Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jun 14 to Jun 15
CA $147
CA $182 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (2,432 reviews)
"Very clean room, had a late check in the staff we waiting with my key and directions at the front desk"
Reviewed on May 30, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Jun 3 to Jun 4
CA $123
CA $179 total
Jun 3 - Jun 4
includes taxes & fees
9/10 Wonderful! (3,458 reviews)
"There was no free Internet. In 2026, how is that possible?. Everything else was very good."
Reviewed on May 30, 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 $115 per night from Jun 2 to Jun 3
CA $115
CA $163 total
Jun 2 - Jun 3
includes taxes & fees
8.8/10 Excellent! (1,721 reviews)
"We’ve stayed in various Colonial Williamsburg properties over the past 50 years. We were disappointed with the Woodlands. The parking lots were filled with potholes and we had to dodge a few to get to our building. The elevator was located off the lobby which required walking a long distance once ..."
Reviewed on May 30, 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.
