Gloucester County Vacations & Trips from $485
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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 destinations in Gloucester County
Gloucester
The Latest Gloucester County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ocean 27
Northeast Virginia Beach
Save 100% on your flight
Price was $1,926, price is now $1,381 per person
$1,381
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
6.4/10 (1,065 reviews)
Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk.
Reviewed on Oct 13, 2025
The Sanderling
Save 100% on your flight
Price was $2,705, price is now $1,948 per person
$1,948
per person
Jun 4 - Jun 11
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (529 reviews)
The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300.
Reviewed on Jan 7, 2026
John Yancey Oceanfront Inn
Price was $804, price is now $585 per person
$585
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
This was by far one of the coolest rooms I’ve ever stayed in. The porch with the Adirondack chairs right there at the sand was just perfect. Everything inside the room was clean and really convenient- plenty of outlets and the right kind of furniture to make the space functional and comfortable.
Reviewed on Mar 19, 2026
Boardwalk Resort and Villas
Northeast Virginia Beach
Save 100% on your flight
Price was $900, price is now $659 per person
$659
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,018 reviews)
We got a suite with ocean view. It was clean and the view was beautiful the next morning on the balcony.
Reviewed on Mar 14, 2026
Find the Best Gloucester County Vacation Packages
Gloucester County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Norfolk Intl. Airport (ORF) |
Top Sights | Middle Peninsula State Park, Gloucester Museum of History and Middle Peninsula State Park |
Gloucester County Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $107 total per night from Mar 22 to Mar 23
$107 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (2,169 reviews)
Don’t get a hot tub room without bringing your own cleaning supplies and hot water
Reviewed on Mar 21, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $134 total per night from Mar 30 to Mar 31
$134 total
Mar 30 - Mar 31
Total with taxes and fees
9/10 Wonderful! (3,412 reviews)
Room was not very clean. Sheets on one bed were dirty, walls were all scuffed up, dorito bag under the couch; just felt dirty. Everything else was amazing.
Reviewed on Mar 20, 2026
Hilton Vacation Club Greensprings Williamsburg
3500 Ludwell Pkwy Williamsburg VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $119 total per night from Mar 29 to Mar 30
$119 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Very pleasant stay. They were very accommodating to our requests. The room was updated and in a great location. Sales pressure was not bad at all and it is a very lovely resort. Will stay again when weather gets warmer.
Reviewed on Mar 18, 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.
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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.
