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.
Kingsmill Resort
Kingsmill
Price was CA $2,191, price is now CA $1,629 per person
CA $1,629
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,019 reviews)
This was our first time at the resort and it was amazing!! Great staff, clean rooms with all of the activities, food and amenities you will need for a relaxing fun stay!! It was our 25th anniversary and we will be back!!
Reviewed on Jun 25, 2026
OYO Hotel Doswell Kings Dominion
Price was CA $1,282, price is now CA $983 per person
CA $983
per person
Aug 15 - Aug 16
found 1 day ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
4/10 (218 reviews)
Rooms were clean and very affordable. I was skeptical at first but had zero issues once I arrived.
Reviewed on Oct 10, 2025
The Commonwealth
Downtown Richmond
Price was CA $1,484, price is now CA $1,147 per person
CA $1,147
per person
Aug 15 - Aug 16
found 1 day ago
Roundtrip flight included
Nanaimo (YCD) to Richmond (RIC)
8.8/10 Excellent! (1,377 reviews)
Location of hotel is excellent , across from the Capitol . Suite was very clean , beautiful bathroom .
i was not happy with the living area , walls were painted dark blue and there was no window . i had expected a view of the Capitol grounds but it was like living in a cage . I believe it false advertising because on line it showed a nice , comfortable , light room with a window .
I was told the hotel was full because of a convention and I could not change to another room .
Reviewed on Jun 25, 2026
Gloucester Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 12 to Jul 13
CA $175
CA $215 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (2,539 reviews)
"We were booked for 6 nights. We arrived later than check-in, got our room and the keys didn’t work => easy fix? We got another set of keys, those didn’t work => still an easy fix => we got a new room. Check in was a little slow…slowwwww. But, I’m from NY/NJ, we are a little faster paced, so maybe ..."
Reviewed on Jun 25, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 9 to Jul 10
CA $132
CA $190 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (3,517 reviews)
"The staff was very friendly and helpful. Property was beautiful and well maintained, lots of amenities."
Reviewed on Jun 25, 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 $122 per night from Jul 19 to Jul 20
CA $122
CA $172 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (1,789 reviews)
"Nice room good location."
Reviewed on Jun 25, 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.
