Gloucester Vacations from $365

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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.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $462, price is now $365 per person
$365
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (299 reviews)
Wonderful property to stay at for our first time in the Williamsbug, VA area. Very clean, quiet, and spacious. The staff at check in was professional & courteous. Contactless checkout was a plus! The only negatives were when the bedroom door was closed, it was a little on the warmer side in the bedroom and the a/c couldn't be turned cooler than 68°. Since we booked online, we were asked if we would be interested in listening to a brief presentation on similar properties with a giftcard & free stay offered for our time. We declined as we were only staying two nights and we weren't sure of what our plans were. When we expressed disinterest, we were asked why we declined and it felt like "No, thank you, not interested" wasn't an acceptable reason. We were not exactly a fan of this part, but overall, a great experience for the short time we were there. Will definitely book again in the future.

Reviewed on Sep 15, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
Price was $1,050, price is now $753 per person
$753
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
10/10 Exceptional! (13 reviews)
Great staff and attitude toward customers.

Reviewed on Aug 3, 2025

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was $564, price is now $431 per person
$431
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (87 reviews)
King's Creek by Spinnaker is a very nice resort. The 2 bedroom cottage was clean and spacious. The staff at check in were very friendly and helpful. We enjoyed our stay and hope to return some day.

Reviewed on Sep 17, 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $670, price is now $527 per person
$527
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
I had an outstanding experience and hope to return in the near future

Reviewed on Sep 17, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $742, price is now $622 per person
$622
per person
Oct 24 - Oct 26
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Richmond (RIC)
9.2/10 Wonderful! (1,176 reviews)
Friendly staff, unique rooms and building

Reviewed on Sep 15, 2025

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Discover the most popular places to visit in Gloucester

Rosewell Ruins

Learn about the local history of Gloucester when you spend time at Rosewell Ruins. Amble around this family-friendly area's picturesque gardens or attend a sporting event.

Rosewell Ruins

Gloucester Museum of History

4/5(1 review)

You can study the exhibits at Gloucester Museum of History, a museum with a storied past, during your trip to Zanoni. Experience the festivals and art scene in this family-friendly area.

Gloucester Museum of History

Gloucester Hotel Deals

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
$86 nightly
The price is $99 total per night from Oct 3 to Oct 4
$99 total
Oct 3 - Oct 4
Total with taxes and fees
9/10 Wonderful! (3,053 reviews)
"This property was absolutely beautiful. The Villa was first class."

Reviewed on Sep 16, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Sep 21 to Sep 22
$104 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (1,730 reviews)
"The rooms nice and comfortable and clean"

Reviewed on Sep 15, 2025

Vacation Village At Williamsburg
Wyndham Garden Williamsburg Busch Gardens Area

Wyndham Garden Williamsburg Busch Gardens Area

3 out of 5
201 Water Country Pkwy, Williamsburg, VA
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Sep 22 to Sep 23
$85 total
Sep 22 - Sep 23
Total with taxes and fees
6.6/10 (320 reviews)
"Great stay"

Reviewed on Sep 15, 2025

Wyndham Garden Williamsburg Busch Gardens Area
See all 2,275 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.

Things to do in and around Gloucester

Gloucester, Virginia, offers a perfect blend of outdoor activities and family-friendly attractions. Enjoy thrilling amusement parks, scenic boardwalks, and recreational areas. For an unforgettable experience, consider Gloucester vacation packages, romantic getaways, popular tours, and ocean adventures, including memorable sailing trips. This charming destination is ideal for creating lasting memories with loved ones amidst beautiful scenery.

Shopping

In Gloucester, you can shop at White Marsh Shopping Center, only 5 miles away, offering a family-friendly vibe. Walter Reed Plaza and Shoppes at Gloucester, both in the area, provide a variety of shops. If you're up for a drive, check out nearby malls for even more options.

Recreation

Gloucester Point Beach Park offers a serene environment for relaxation, perfect for unwinding by the water. Kiskiack Golf Club provides a scenic outdoor experience for golf enthusiasts, while Waller Mill Park invites you to enjoy nature trails and peaceful surroundings for a refreshing wellness escape.

Adventure

Experience thrilling water rides at Water Country USA, located 12 miles from Gloucester, perfect for family fun and adventure. Alternatively, dive into excitement at MagiQuest, an immersive arcadeAdventureZone also 12 miles away, or bounce around at Bounce House, an arcadeAdventureZone situated 13 miles from Gloucester, offering endless family-friendly activities.

Nightlife

In Gloucester, Virginia, experience a laid-back nightlife with cozy bars and local eateries. Visit the historic downtown for live music and craft beer at venues like The Coffee Spot, or unwind at a waterfront restaurant for stunning views and relaxed vibes along the York River.

*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 an ideal destination for outdoor and family vacations, offering scenic beauty and a variety of attractions. Visitors can explore the Gloucester Docks, admire the historic Gloucester Cathedral, enjoy a relaxing day at Gloucester Beach, or discover local charm at Gloucester Quays. With its mix of islands and beaches, Gloucester promises a delightful experience for those seeking adventure and relaxation in a picturesque setting.

  • Yorktown Beach: Located 12 miles from Gloucester, Yorktown Beach offers a relaxing seaside experience with stunning views of the York River. Enjoy sandy shores, gentle waves, and a family-friendly atmosphere perfect for swimming, picnicking, or simply soaking up the sun.
  • Rosewell Ruins: Situated within Gloucester, the Rosewell Ruins are a fascinating glimpse into the area's colonial past. Explore the remnants of this once-grand plantation house, which showcase unique architecture and historical significance, inviting you to reflect on the region's rich culture.
  • Gloucester Museum of History: Also located in Gloucester, this museum provides an engaging overview of the area's local history. Through exhibits and artifacts, discover the stories that shaped Gloucester, offering a deeper understanding of its community and heritage.

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 during the off-peak season (typically January to March) for more affordable package holidays to Gloucester.
  • 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.

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Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from $365 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.