Gloucester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Kingsmill Resort
Whispering Pines by Hotel O Whitestone VA
Kings Creek Plantation by TripForth
King’s Creek Resort by Spinnaker

Ready to book your vacation to Gloucester?

 

Choose your dates

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 $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (697 reviews)
"They didn't clean the room every day."

Reviewed on May 8, 2026

Holiday Inn Express Gloucester by IHG
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 $117 per night from Jun 1 to Jun 2
CA $117
CA $150 total
Jun 1 - Jun 2
includes taxes & fees
8.8/10 Excellent! (2,416 reviews)
"The gate to the entrance was still open which seemed to result in many cars/people enter for what appeared to be a party woth 70-100 people and cars zipping around property. This went on for quite some time. I witnessed cars speeding around the parking area resulting in two vehicle hitting each other. ..."

Reviewed on May 18, 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 $127 per night from Jun 2 to Jun 3
CA $127
CA $184 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (3,485 reviews)
"We had a great time Everyone was very friendly and a lot to do on the property. They had a great assortment of pools to go into, miniature golf, tennis etc.. and the property was very nice to walk around and relax. The Restaraunt had great meals with great prices (especially for breakfast). We were ..."

Reviewed on May 19, 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.