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.
Whispering Pines by Hotel O Whitestone VA
Price was CA $972, price is now CA $856 per person
CA $856
per person
Jul 23 - Jul 27
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6.2/10 (157 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
Holiday Inn Express Williamsbrg Busch Gardens Area by IHG
Price was CA $1,195, price is now CA $1,059 per person
CA $1,059
per person
Jul 27 - Jul 31
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,235 reviews)
Nice rooms breakfast was great
Reviewed on Jun 15, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,052, price is now CA $955 per person
CA $955
per person
Jul 27 - Jul 31
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,780 reviews)
This is a large spread out facility. There is a lot of walking to get to the pool or to “breakfast”, which was nothing but bagels and muffins and cereal.
Reviewed on Jun 18, 2026
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,198, price is now CA $1,096 per person
CA $1,096
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.2/10 Very Good! (1,011 reviews)
Great staff! Great downtown location! Clean and quiet.
Reviewed on Jun 4, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $147 per night from Jun 28 to Jun 29
CA $147
CA $164 total
Jun 28 - Jun 29
includes taxes & fees
7.2/10 Good! (708 reviews)
"Great room shower water gets really hot. The elevator was the only drawback . Its old and jerked a bit .. outside of that my stay was perfect"
Reviewed on Jun 19, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Jun 30 to Jul 1
CA $209
CA $252 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (2,520 reviews)
"It was excellent for the family and 5 suites I reserved! Check in and check out went very smoothly!"
Reviewed on Jun 19, 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 Jun 22 to Jun 23
CA $131
CA $189 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (3,495 reviews)
"The resort is terrific but the check in process was so painful. The line was literally an hour long for 5 hours! They need to improve efficiency in a big way!"
Reviewed on Jun 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.
