Gloucester Vacations

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Find the Best Gloucester Vacation Packages

Gloucester Hotel Deals

Hampton Inn Gloucester

Hampton Inn Gloucester

6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
NT$3,127
NT$3,480 total
Sep 20 - Sep 21
includes taxes & fees
9.2/10 Wonderful! (796 reviews)
"Keri and her staff were terrific, they were all very friendly and helpful. Breakfasts were very good. Even though there is renovation work in progress - it was no where near as intrusive, noise or otherwise, as I thought it might be as when we read the postings when we arrived."

Reviewed on 2026/9/9

Hampton Inn Gloucester
Vacation Village At Williamsburg

Vacation Village At Williamsburg

4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
NT$2,742
NT$3,486 total
Sep 24 - Sep 25
includes taxes & fees
Vacation Village At Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
NT$2,113
NT$3,310 total
Sep 13 - Sep 14
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,260 properties in Gloucester
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.
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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.
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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.
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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.
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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.
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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.
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Gloucester Public Library

Gloucester Public Library is just one of the places to see in Gloucester, so why not enjoy the other things to explore during your travels? Experience the festivals and art scene in this family-friendly area.
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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+ artifacts. Explore American Revolution and Civil War exhibits while enjoying free admission to this historic treasure.
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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?
  1. 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.
  2. 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.
  3. 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.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Gloucester vacation package for you.

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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.