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.
Ashland Studio Inn By OYO Richmond North near Kings Dominion
Turnpike Motel Richmond VA by Hotel O US 60
King’s Creek Resort by Spinnaker
A house full of steel balls and games
Lisa's Ranch

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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 $169 per night from Jun 18 to Jun 19
CA $169
CA $207 total
Jun 18 - Jun 19
includes taxes & fees
8.8/10 Excellent! (2,502 reviews)
"Very affordable price for a 2 bedroom apartment. Could definitely use some updating- they said our unit was remodeled 4 years ago but the color and decor says it was more likely in the 1990’s. Overall clean and convenient."

Reviewed on Jun 14, 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 $130 per night from Jun 17 to Jun 18
CA $130
CA $187 total
Jun 17 - Jun 18
includes taxes & fees
9/10 Wonderful! (3,521 reviews)
"very outdated, shows it age, very slow and inefficient check-in"

Reviewed on Jun 14, 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
The price is CA $125 per night from Jun 30 to Jul 1
CA $125
CA $176 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,774 reviews)
"This hotel is wonderful. The staff is exceptionally helpful and friendly. It is conveniently located. The landscaping is absolutely gorgeous. There are family friendly amenities all around the property, and the price is right! I will definitely be staying here when I return to Williamsburg."

Reviewed on Jun 14, 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.

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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.