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.
Motel 6 Sandston, VA - Richmond, Va
Price was CA $1,366, price is now CA $1,055 per person
CA $1,055
per person
Aug 14 - Aug 16
found 12 hours ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
7.8/10 Good! (1,053 reviews)
It was a little shady however the inside was clean, the bed n pillows were comfortable and the room was the coldest room I’ve ever slept in! I would go back to Virginia just to stay in that cold room!
Reviewed on Jun 22, 2026
The Commonwealth
Downtown Richmond
Price was CA $1,732, price is now CA $1,329 per person
CA $1,329
per person
Aug 14 - Aug 16
found 12 hours ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
8.8/10 Excellent! (1,377 reviews)
For an older property, this hotel is very well-maintained. The staff are very friendly and accommodating. Our dog loved this hotel and the park across the street!
Reviewed on Jun 20, 2026
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,766, price is now CA $1,362 per person
CA $1,362
per person
Aug 14 - Aug 16
found 12 hours ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
8.2/10 Very good! (1,011 reviews)
Great staff! Great downtown location! Clean and quiet.
Reviewed on Jun 4, 2026
Four Points by Sheraton Richmond
North Chesterfield
Price was CA $1,511, price is now CA $1,174 per person
CA $1,174
per person
Aug 14 - Aug 16
found 11 hours ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
8.8/10 Excellent! (1,021 reviews)
Enjoyed my stay, rooms and property were well kept no complaints.
Reviewed on Jun 22, 2026
Gloucester Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 22 to Jul 23
CA $174
CA $214 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (2,530 reviews)
"Honestly, we were disappointed this year. We've been coming every year for the last 4 summers, and it seems like it has gotten worse every year. This year, they initially didnt have a room for our reservation and when they did find a room, it was as if someone had used it. The toilet was dirty, the ..."
Reviewed on Jun 23, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $148 per night from Jun 30 to Jul 1
CA $148
CA $208 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (3,507 reviews)
"We loved all the activities available to us. Really felt like home. We also appreciate how accommodating you were to us."
Reviewed on Jun 23, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
The price is CA $118 per night from Jul 20 to Jul 21
CA $118
CA $168 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,781 reviews)
"The hotel is a bit dated for the price. The rooms could use a face lift. The complimentary breakfast is helpful, but the offerings are very basic and it gets very, very crowded in the breakfast area making it hard to find seating and to get food. Our room wasn't ready at 4:00 and everyone else checking ..."
Reviewed on Jun 23, 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.
