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
Wedmore Place
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Hilton Richmond Downtown
The Commonwealth

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Gloucester Hotel Deals

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jul 23 to Jul 24
CA $194
CA $236 total
Jul 23 - Jul 24
includes taxes & fees
8.8/10 Excellent! (2,540 reviews)
"3 stars max"

Reviewed on Jun 26, 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
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 15 to Jul 16
CA $131
CA $190 total
Jul 15 - Jul 16
includes taxes & fees
9/10 Wonderful! (3,518 reviews)
"Great place very big and beautiful. Great staff!"

Reviewed on Jun 25, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
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! (1,779 reviews)
"Nice room good location."

Reviewed on Jun 25, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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.