Gloucester County Holidays
Book a Hotel + Flight or Car together to unlock savings
Top destinations in Gloucester County
Top hotels in Gloucester County
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
1.908.680 ₫
2.481.912 ₫ total
30 Aug - 31 Aug
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
1.750.936 ₫
2.743.298 ₫ total
9 Sept - 10 Sept
includes taxes & fees
9.2/10 Wonderful! (3,755 reviews)
"The property overall was a good place to stay. We rented a two story, 4 bedroom townhouse with 4 bathrooms. The downstairs master bathroom was missing a shower curtain. After calling the front desk I was told that someone would be over to install a new one. After a while, I finally received a knock ..."
Reviewed on 14 Aug 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
2.156.403 ₫
3.068.767 ₫ total
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (1,919 reviews)
"Great family hotel! Huge pool, water play area, put put golf, pingpong, volleyball, kids playground, and complimentary breakfast, and more! No alcohol sales on property so bring your own. I will re-book!!"
Reviewed on 14 Aug 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 holiday package cost?
Starting from just , 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 holiday 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 1null000null000 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 holiday?
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 travelling 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 holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday 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 holiday package?
If your holiday 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?
Gloucester Museum of History
9.0/10 (4 reviews)
You can study the exhibits at Gloucester Museum of History, a museum with a storied past, during your trip to Gloucester. Experience the festivals and art scene in this family-friendly 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.
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.
Machicomoco State Park
You can take time to visit Machicomoco State Park during your travels to Hayes. Make some time to visit the shops while you're in the area.
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.
Jordan Marina
Explore the waterfront in Gloucester Point with a trip to Jordan Marina.
