Gloucester County Vacation Packages
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Your Gloucester County Vacation
Make organizing your next big adventure a breeze with a Gloucester County vacation package. Whether it's the history, cuisine or something else that brings you to this destination, our package deals will help you experience it all. Start your trip to Gloucester County by spending a few days in Gloucester, one of the best cities here. Expedia is a one-stop shop for planning your Gloucester County vacation. From hotels and flights, to activities and more, we know how to curate a travel experience like no other.
Top Gloucester County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Blackbeard's Lodge
CA $1,341
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.4/10 Very good! (384 reviews)
Blackbeard's is an older hotel very conveniently located on the island. maintenance lacks. Ice maker broken, faucets are loose etc. The staff, Cynthia, was very helpful and responsive.
Reviewed on Aug 23, 2026
Pony Island Inn
CA $1,423
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
9.4/10 Exceptional! (489 reviews)
This is a very charming spot to power down from a day filled with Ocrakokean fun.
Perfectly located. Extremely friendly staff.
Reviewed on Aug 24, 2026
Gloucester County Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $120
CA $152 total
Sep 9 - Sep 10
includes taxes & fees
8.8/10 Excellent! (2,813 reviews)
"This place was amazing, clean, everyone was nice. The suite was exceptional, everyone had their own space. It was wonderful, I would definitely recommend it for a family , my granddaughters loved it."
Reviewed on Aug 24, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $92
CA $145 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (3,822 reviews)
"Everything included and an amazing location. Everything is 5-10 minutes from the resort. It was the Perfect stay and we will be back!! Room was also very clean and comfortable with a lot of space!"
Reviewed on Aug 24, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $106
CA $153 total
Sep 21 - Sep 22
includes taxes & fees
8.8/10 Excellent! (1,973 reviews)
"Room was very comfortable having the outside quarters in the suite was excellent for couples where one was up earlier than the other"
Reviewed on Aug 24, 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.
Frequently asked questions
How much does a Gloucester County vacation package cost?
Starting from just CA $1,016, a package is your portal to cheaper travel. Put together your Gloucester County getaway by picking from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Gloucester County?
Book everything in the one place with our Gloucester County vacation packages. We have deals on flights, hotels and more that'll keep your pocket happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 hotel options around the globe to choose from, there are endless opportunities to mix and match as you like.
What are the top hotels in Gloucester County?
For properties in Gloucester with comfy beds and friendly service, you can't beat Holiday Inn Express Gloucester, an IHG Hotel and Hampton Inn Gloucester. If you plan to visit Hayes as well, you can look forward to a solid night's sleep at Chesapeake Bay Rv Resort Thousand Trails or Waterfront Cottage With Pool.
How far in advance should I book my Gloucester County vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, discount tickets to Gloucester County sometimes emerge a few weeks before departure.
What does an Expedia Gloucester County travel package include?
It comes down to what you're looking for. If you're traveling solo, you might decide to combine flights and hotels. Taking the entire family to Gloucester County? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the flexibility to build your own travel package.
What should I know before booking a Gloucester County travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on activities or tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Gloucester County Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Gloucester County vacation package?
If your vacation plans in Gloucester County have been upended, it's good to know that it's possible to cancel or amend your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose fees. To learn more, check our Customer Service Portal.
Stay near popular Gloucester County attractions
Cuba Island
Commune with nature and explore the great outdoors at Cuba Island during your travels in Hayes. Make some time to visit the shops while you're in the area.
Gloucester Point Beach Park
Gloucester Point Beach Park is just one of the places to see in Gloucester Point, so why not enjoy the other things to explore during your travels?
Middle Peninsula State Park
10.0/10 (1 review)
You can take time to visit Middle Peninsula State Park during your travels to Gloucester. Experience the festivals and art scene in this family-friendly area.
Rosewell Ruin and Visitor Center
6.0/10 (2 reviews)
Learn about the local history of Gloucester when you spend time at Rosewell Ruin and Visitor Center. Amble around this family-friendly area's picturesque gardens or attend a sporting event.
Jordan Marina
Explore the waterfront in Gloucester Point with a trip to Jordan Marina.
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.
Jordan Island
Commune with nature and explore the great outdoors at Jordan Island during your travels in Hayes. Make some time to visit the shops while you're in the area.
Carmines Islands
Commune with nature and explore the great outdoors at Carmines Islands during your travels in Hayes. Make some time to visit the shops while you're in the area.
What to do in Gloucester County
Colonial Williamsburg Admission
CA $54
per adult
88% of travellers recommend
Jamestown Settlement American Revolution Museum 7-Day Ticket
CA $41
per adult
100% of travellers recommend
Williamsburg Ghosts, Witches and Pirates Tour
CA $35
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
