Gloucester Point Vacations from $448

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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 $631, price is now $448 per person
$448
per person
Jun 2 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,884 reviews)
Clean room, kind staff, great location

Reviewed on Mar 5, 2026

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,213, price is now $819 per person
$819
per person
Jun 2 - Jun 5
found 1 day 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

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $1,646, price is now $1,121 per person
$1,121
per person
May 22 - May 26
just found
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
Very friendly staff. Lots of amenities, however restaurant was closed for the season.

Reviewed on Mar 2, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $950, price is now $656 per person
$656
per person
Jun 2 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (23 reviews)
beautiful room with very responsive concierge

Reviewed on Jan 15, 2026

The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $915, price is now $660 per person
$660
per person
Jun 2 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.6/10 Exceptional! (27 reviews)
What a gorgeous property- conveniently located, close to the beaches and all types of activities. We couldn’t have been happier. Andrew and Julie G.

Reviewed on Sep 1, 2025

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Discover the most popular places to visit in Gloucester Point

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 Point Beach Park

What to do in Gloucester Point

See these Tall Ships up close!

Jamestown Settlement American Revolution Museum 7-Day Ticket

$29
per adult
100% of travellers recommend
Jamestown Settlement American Revolution Museum 7-Day Ticket
Reviewing photos and stories about Williamsburg Before and After

Private Colonial Williamsburg Breakfast - Exploring Before and After Restoration

$75
per adult
Private Colonial Williamsburg Breakfast - Exploring Before and After Restoration
People enjoy history of Battle Capes and Siege of Yorktown, 1781.

Let's Go Sail Virginia

$96
per adult
100% of travellers recommend
Let's Go Sail Virginia
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
$122 nightly
The price is $139 total per night from Mar 22 to Mar 23
$139 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (3,411 reviews)
I love the Powhatan. It has been my home away from home for years. Everyone is always friendly and caring. We have the amenities as if we were home. I love it!

Reviewed on Mar 6, 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
$81 nightly
The price is $93 total per night from Mar 22 to Mar 23
$93 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (2,133 reviews)
Older

Reviewed on Mar 6, 2026

Vacation Village At Williamsburg
Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
1905 Coliseum Dr Hampton VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Apr 5 to Apr 6
$116 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,336 reviews)
Great location

Reviewed on Mar 6, 2026

Hyatt Place Hampton Convention Center
See all 1,907 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 $448 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.