Gloucester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Gloucester Holiday
Our pick of the best Gloucester Hotel Deals
Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
NZ$198
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (799 reviews)
"The staff was excellent!!"
Reviewed on 17 Sept 2026
Perfect for long-term workers & short stays—comfort, style & convenience await!
Gloucester VA
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
NZ$184
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (3,847 reviews)
"September 12, 2026 We just stayed one night passing through Williamsburg. Everyone that we encountered was extremely nice and helpful. The room was very comfortable and clean. It’s more than just a place to stay. It’s a resort. DH"
Reviewed on 18 Sept 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.
Stay near popular Gloucester attractions
Beaverdam Park
Explore Beaverdam Park's 635-acre reservoir through hiking trails and tranquil waterways. Rent a boat to fish for largemouth bass or observe diverse wildlife from the park's scenic overlooks.
Middle Peninsula State Park
10.0/10 (1 review)
Virginia's first state park dedicated to Native American history showcases the legacy of the Powhatan Confederacy. Explore interpretive exhibits, scenic trails, and diverse habitats from tidal marshes to mixed forests.
Rosewell Ruin and Visitor Center
6.0/10 (2 reviews)
These haunting brick ruins were once America's grandest colonial mansion, built by the Page family in 1725. Explore the massive chimneys and remaining walls while overlooking the serene York River landscape.
Shoppes at Gloucester
You can do some window-shopping at Shoppes at Gloucester during your trip to Gloucester. Experience the festivals and art scene in this family-friendly area.
Thousand Trails Beach Park
This 280-acre waterfront campground offers shaded RV sites and cabins along Virginia's Piankatank River. Enjoy fishing, mini-golf, and seasonal events while exploring nearby historical attractions in Gloucester.
Gloucester Golf Club
This classic 9-hole parkland course has welcomed golfers of all skill levels since 1929. Enjoy the relaxed atmosphere while navigating well-maintained fairways and challenging greens at this local favourite.
Main Street Center
You can find the perfect gifts to bring home at Main Street Center during your visit to Gloucester. Experience the festivals and art scene in this family-friendly area.
Gloucester Museum of History
9.0/10 (4 reviews)
Housed in the 1770 Botetourt Building, this museum displays Gloucester County's rich past through 3,000+ artefacts. Explore American Revolution and Civil War exhibits while enjoying free admission to this historic treasure.
Frequently asked questions
How much does a Gloucester holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Gloucester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
If you'd like to book a cheap Gloucester holiday package, consider planning a trip in January, February and April. You're likely to find lower prices on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Gloucester?
Typically, a handful of days is enough to check out the major attractions during your Gloucester holiday. However, if you want to have more time to kick back or take day tours, consider extending your itinerary.
How to find the best Gloucester package deals?
Start your search for a Gloucester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gloucester package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gloucester escape off to a flying start.
Is it cheaper to book a Gloucester holiday as a package?
You can enjoy significant savings on your Gloucester retreat by booking a customised holiday package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Gloucester?
If you're considering a spontaneous Gloucester holiday, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Gloucester?
- Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Gloucester.
- Set your budget: Factor in costs like flights, transportation and food when calculating how much to save for your trip to Gloucester. Then, pick a property that fits your budget, whether that's an economical option or a swankier getaway.
- Decide your trip length: Think about how much time you want to spend exploring Gloucester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your accommodation and airfare: After you've nailed down your trip dates and duration, book the right Gloucester holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
