Gloucester Vacations from $315

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Your Gloucester Vacation

From its coastal scenery to its rich history and beyond, there's loads to like about Gloucester. Discover the wonders of this captivating city with a Gloucester vacation package that's made for you. Eager to do a bit of sightseeing? A trip to Gloucester isn't complete without checking out Middle Peninsula State Park, Gloucester Museum of History and other major attractions. Your Gloucester vacation is clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Gloucester vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort
The Colonies at Williamsburg
Linden Row Inn
Barsala At Sphere Apartments
Club Wyndham Kingsgate
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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
Holiday Inn Express Gloucester by IHG
3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
$111 nightly
The price is $124 total per night from Jul 13 to Jul 14
$124 total
Jul 13 - Jul 14
Total includes taxes and fees
7/10 Good! (616 reviews)
"Sunday we didn't have hot water so we couldn't take showers."

Reviewed on Jun 30, 2025

Holiday Inn Express Gloucester by IHG
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
$118 nightly
The price is $134 total per night from Jul 13 to Jul 14
$134 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (2,797 reviews)
"The area was peaceful. The room was clean and huge! Front desk could use a few more people working since it took us 20mins to check in. Wifi was ok. Overall would stay again for vacation."

Reviewed on Jul 4, 2025

Hilton Vacation Club The Historic Powhatan 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
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $127 total per night from Jul 7 to Jul 8
$127 total
Jul 7 - Jul 8
Total includes taxes and fees
8.8/10 Excellent! (1,420 reviews)
Woodlands
"This is our second stay at the Woodlands, last time was December 2024. The convenience to the Visitor Center, downtown and shuttle is AMAZING. We have walked numerous times but this time took the shuttle since it was raining. 1000% recommend because of this. The breakfast in the morning was great ..."

Reviewed on Jul 3, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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 Vacation Packages

Gloucester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Newport News - Williamsburg Intl. Airport (PHF)
Population
3,000
Max Temp Winter
50ºF
Max Temp Summer
85ºF
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 vacation package cost?
Offering great value package deals from $315 on Expedia, you'll be pleasantly surprised at how much a vacation to Gloucester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
If you're hoping to snag a cheap Gloucester vacation package, consider visiting in November, December and January. You'll typically find lower prices on accommodations and flights during these months --- ideal for travelers wishing to save money.
How many days is enough for Gloucester?
Generally, a handful of days is enough to explore the main sights during your Gloucester vacation. However, if you prefer to have some time to unwind or go on day tours, think about extending your itinerary.
How to find the best Gloucester package deals?
Start your search for a Gloucester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gloucester package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gloucester escape off to a flying start.
Is it cheaper to book a Gloucester vacation as a package?
You can enjoy significant savings on your Gloucester retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Gloucester?
If you're considering a spontaneous Gloucester vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Gloucester vacation packages?
Your Gloucester break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.