Gloucester Point Vacations from $682

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The Latest Gloucester Point vacation packages

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $914, price is now $682 per person
$682
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (1,955 reviews)

The Historic Cavalier Hotel and Beach Club, Autograph Collection

The Historic Cavalier Hotel and Beach Club, Autograph Collection

4 out of 5
Northeast Virginia Beach
Price was $1,987, price is now $1,567 per person
$1,567
per person
Dec 28 - Jan 2
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (410 reviews)

The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $1,453, price is now $1,158 per person
$1,158
per person
Dec 28 - Jan 2
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
10/10 Exceptional! (114 reviews)
We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn. The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets. I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!

Reviewed on Oct 20, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $887, price is now $707 per person
$707
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,005 reviews)

Ocean Pines Resort

Ocean Pines Resort

3.5 out of 5
Price was $1,024, price is now $818 per person
$818
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (162 reviews)
Perfect location and enjoyable stay

Reviewed on Oct 11, 2026

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Stay near popular Gloucester Point attractions

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?
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What to do in Gloucester Point

Jamestown Settlement American Revolution Museum 7-Day Ticket

Jamestown Settlement American Revolution Museum 7-Day Ticket

$29
per adult
100% of travellers recommend
Jamestown Settlement American Revolution Museum 7-Day Ticket
Speak Easy Murder Mystery Dinner Show at Kings Creek Williamsburg

Speak Easy Murder Mystery Dinner Show at Kings Creek Williamsburg

$55
per adult
100% of travellers recommend
Speak Easy Murder Mystery Dinner Show at Kings Creek Williamsburg
Virginia: speakeasy-themed murder mystery dinner at King ́s C

Virginia: speakeasy-themed murder mystery dinner at King ́s C

$60
per adult
Virginia: speakeasy-themed murder mystery dinner at King ́s C
See all activities in Gloucester Point

Gloucester Point 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
$92 nightly
The price is $105 total per night from Nov 2 to Nov 3
$105 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (4,004 reviews)
"Was a great place - clean, personnel was always helpful and quick to get back to you. Close to it all as well!"

Reviewed on Oct 27, 2026

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
$124 nightly
The price is $141 total per night from Nov 9 to Nov 10
$141 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (3,027 reviews)
"Very clean and spacious."

Reviewed on Oct 26, 2026

Vacation Village At Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr Williamsburg VA
$117 nightly
The price is $132 total per night from Oct 29 to Oct 30
$132 total
Oct 29 - Oct 30
Total with taxes and fees
8.8/10 Excellent! (2,054 reviews)
"Close to all of the attractions"

Reviewed on Oct 26, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,214 properties in Gloucester Point
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 Point Vacation Packages

Gloucester Point Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
9,400
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 Point vacation package cost?
Offering great value package deals from $682 on Expedia, you'll be thrilled with how little a vacation to Gloucester Point costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester Point?
November, December and January are great times to search for cheap Gloucester Point vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Gloucester Point?
With a well-planned itinerary, you can easily visit the top Gloucester Point sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Gloucester Point vacation for longer.
How to find the best Gloucester Point package deals?
Landing a cheap Gloucester Point package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Gloucester Point package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Gloucester Point vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Gloucester Point vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Gloucester Point?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Gloucester Point getaway.
How to plan a trip to Gloucester Point?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Gloucester Point.
  2. Budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Gloucester Point.
  3. Organize your Gloucester Point escape with our trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Gloucester Point together.
  4. Work out your trip length: Think about how much time you'd like to spend exploring Gloucester Point. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Gloucester Point vacation package.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the highlights of Gloucester Point. Find all the incredible things to do in Gloucester Point with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Gloucester Point vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Gloucester Point trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.