Gloucester Vacation Packages 2026 from $469

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.

The Latest Gloucester vacation packages

Price found within the past 48 hours. Click for updated prices.

The Colonies at Williamsburg

$469

per person

Nov 24 - Nov 27

found 4 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

9/10 Wonderful! (1,041 reviews)

Staff at check in were nice and helpful. As soon as we got into our room I noticed someone's wallet. I called the front desk and let them know. Said we'd bring it in the morning since we checked in at 11 pm. They called our room at 2 am asking if the person could come right then and pick up their wallet. We also noticed that the bathroom floor had spots all the around the toilet, the sink was on and the sink was halfway full. The stovetop was dirty and cob webs all around the light fixture above the dining room table. We let them know and the lady said they'd have someone come clean but never did.

Reviewed on Aug 31, 2026

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$494

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,002 reviews)

Lovely spot that was very close to where I needed to be so could walk. Rooms were clean with a full kitchen. Comfortable beds, nice A/C, great fitness room. It's more of a "motel" so people are walking by your room so curtains can't be opened unless you want everybody to see in.

Reviewed on Aug 23, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$586

per person

Nov 24 - Nov 27

found 3 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.8/10 Excellent! (868 reviews)

Holiday Inn Hotel and Suites Richmond West End by IHG

Laurel

$585

per person

Oct 3 - Oct 10

found 13 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.8/10 Excellent! (606 reviews)

😊

Reviewed on Aug 31, 2026

Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

$517

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8/10 Very Good! (1,000 reviews)

one bedroom suite was helpful to insulate noise.

Reviewed on Aug 30, 2026

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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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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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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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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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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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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.

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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

6639 Forest Hill Ave Gloucester VA

Fully refundable

$91 nightly

$101 total

Sep 3 - Sep 4

Total with taxes and fees

Vacation Village At Williamsburg

4870 Longhill Road Williamsburg VA

Fully refundableReserve now, pay when you stay

$107 nightly

$122 total

Sep 14 - Sep 15

Total with taxes and fees

8.8/10 Excellent! (2,836 reviews)

"Nice place, would go and stay here again."

Reviewed on Aug 31, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA

Fully refundableReserve now, pay when you stay

$92 nightly

$105 total

Sep 8 - Sep 9

Total with taxes and fees

9.2/10 Wonderful! (3,784 reviews)

"Clean and comfy beds! however the covers looked past its expiration date. batteries were missing from remote. clean well maintained pools! bartender at poolside bar is awesome! i will definitely stay here again! loved the set up of the rooms"

Reviewed on Aug 30, 2026

See all 2,255 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.

Find the Best Gloucester Vacation Packages

Things to do in and around Gloucester

Gloucester, Virginia, offers a delightful mix of outdoor and family-friendly activities, perfect for a scenic vacation. Enjoy thrilling rides at the amusement park, stroll along the boardwalk, or relax in the recreational areas. For an unforgettable experience, consider exploring vacation packages, romantic getaways, popular tours, and ocean adventures, including memorable sailing trips.

Shopping

For shopping in Gloucester, visit White Marsh Shopping Center, just 5 miles away, offering a mix of family and city vibes. In the heart of Gloucester, check out Walter Reed Plaza and Main Street Center, both providing a diverse shopping experience with a friendly atmosphere.

Recreation

Gloucester Point Beach Park offers a tranquil coastal retreat with sandy shores and scenic views, perfect for relaxation. Kiskiack Golf Club invites you to enjoy a round of golf amidst beautiful landscapes, while Waller Mill Park provides serene walking trails and peaceful green spaces for rejuvenation.

Adventure

Experience thrilling water slides and wave pools at Water Country USA, located 12 miles from Gloucester. Dive into the fun at MagiQuest, an exciting arcade adventure zone, also 12 miles away. For more family fun, bounce around at the Bounce House, situated 13 miles from Gloucester.

Nightlife

In Gloucester, Virginia, enjoy a relaxed nightlife with local pubs and restaurants offering live music and friendly atmospheres. Visit venues like The White Dog Bistro for a casual meal or explore nearby taverns for drinks and conversation, all while soaking in the charm of this historic town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Gloucester

Gloucester, Virginia, is perfect for outdoor family vacations, offering beautiful scenery and a variety of attractions. Explore local points of interest, including Gloucester Beach, the historic Gloucester Cathedral, and the scenic Gloucester Docks and Quays. Whether you're looking to relax on the beach or discover the rich culture of the area, Gloucester has something for everyone to enjoy.

Yorktown Beach: Located 12 miles from Gloucester, Yorktown Beach offers a stunning waterfront experience with soft sands and beautiful views of the Chesapeake Bay. It's the perfect spot for relaxation, beach activities, and picnics with family and friends.
Rosewell Ruins: Nestled within Gloucester, the Rosewell Ruins are a glimpse into 18th-century architecture and history. This site showcases the remnants of a once-grand mansion, surrounded by lush greenery, making it a serene location for history enthusiasts and photographers alike.
Gloucester Museum of History: Situated in the heart of Gloucester, this museum offers a rich exploration of the area's history through engaging exhibits and artifacts. Visitors can learn about local heritage and culture, making it a must-see for those interested in the past.

Tips to save on your trip to Gloucester

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Gloucester during the low season (January to March) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Gloucester Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Newport News - Williamsburg Intl. Airport (PHF)
Population	3,000
Max Temp Winter	50ºF
Max Temp Summer	85ºF
Top Sights	Gloucester Museum of History, Middle Peninsula State Park and Rosewell Ruins

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Frequently asked questions

How much does a Gloucester vacation package cost?

Offering great value package deals from $469 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're hoping to snag a cheap Gloucester vacation package, consider visiting in November, December and January. You'll typically find lower prices on accommodations and flights during these months — ideal for travelers wishing to save money.

How many days is enough for Gloucester?

Generally, a handful of days is enough to explore the main sights during your Gloucester vacation. However, if you prefer to have some time to unwind or go on day tours, think about 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.

Does Expedia offer Book Now, Pay Later Gloucester vacation packages?

Your Gloucester break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.

Gloucester Vacations from $469

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Your Gloucester Vacation

The Latest Gloucester vacation packages

The Colonies at Williamsburg

Westgate Historic Williamsburg Resort

Griffin Hotel, an official Colonial Williamsburg Hotel

Holiday Inn Hotel and Suites Richmond West End by IHG

Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

Stay near popular Gloucester attractions

Beaverdam Park

Middle Peninsula State Park

Rosewell Ruin and Visitor Center

Shoppes at Gloucester

Purtan Island

Gloucester Museum of History

Main Street Center

Gloucester Golf Club

Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Vacation Village At Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

Find the Best Gloucester Vacation Packages

Things to do in and around Gloucester

Find the best attractions in and around Gloucester

Tips to save on your trip to Gloucester

Gloucester Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia