Gloucester Vacations
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Find the Best Gloucester Vacation Packages
Gloucester Hotel Deals
Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
￥16,793
￥18,691 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (799 reviews)
"The staff was excellent!!"
Reviewed on Sep 17, 2026
Warner Hall
4750 Warner Hall Road Gloucester VA
￥34,205
￥38,069 total
Sep 29 - Sep 30
includes taxes & fees
10/10 Exceptional! (43 reviews)
"The historical significance of this property is reason alone to visit. George Washington's great grandfather established a plantation there in 1642. While original buildings were burned, the owners have restored according to drawings and records. There's a cemetery on property with graves from 1600s. ..."
Reviewed on Sep 19, 2026
Perfect for long-term workers & short stays—comfort, style & convenience await!
Gloucester VA
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.
Purtan Island
This untouched Chesapeake Bay island offers pristine coastal ecosystems in a natural setting. Access requires private boating arrangements, rewarding visitors with serene landscapes far from developed shores.
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.
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.
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.
Main Street Center
You can do some window-shopping at Main Street Center during your stay in Gloucester. Experience the festivals and art scene in this family-friendly area.
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 favorite.
Frequently asked questions
How much does a Gloucester vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 travelers 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 vacation. 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 vacation as a package?
You can enjoy significant savings on your Gloucester retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Gloucester?
If you're considering a spontaneous Gloucester vacation, 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 accommodations and airfare: After you've nailed down your trip dates and duration, book the right Gloucester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
