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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
The Commonwealth
Kingsmill Resort
Turnpike Motel Richmond VA by Hotel O US 60
Lisa's Ranch

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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $140 per night from Jul 16 to Jul 17
CA $140
CA $156 total
Jul 16 - Jul 17
includes taxes & fees
7.2/10 Good! (707 reviews)
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."

Reviewed on Jun 9, 2026

Holiday Inn Express Gloucester by IHG
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
The price is CA $186 per night from Jun 30 to Jul 1
CA $186
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (2,507 reviews)
"Great place to stay with family"

Reviewed on Jun 16, 2026

Vacation Village At Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
The price is CA $130 per night from Jun 22 to Jun 23
CA $130
CA $187 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (3,531 reviews)
"Big spacious rooms great staff and in a great location to do things outside of the club if need be"

Reviewed on Jun 16, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
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.

Stay near popular Gloucester attractions

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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.