Gloucester Vacations

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Find the Best Gloucester Vacation Packages

Gloucester Hotel Deals

Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is ￥14,784 per night from Aug 10 to Aug 11
￥14,784
￥16,454 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (706 reviews)
"Fantastic"

Reviewed on Jul 31, 2025

Hampton Inn Gloucester
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
The price is ￥12,339 per night from Aug 12 to Aug 13
￥12,339
￥18,241 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (2,905 reviews)
Poor check-in time and restaurant not open
"We arrived around 5pm on Thursday the 24th of July 2025. There was a queue at check-in and it took for aged to reach the counter. Secondly we asked whether the resport had a restaurant, as we were not going out to eat nor make food in the kitchen. The answer was yes and that it closed at 9.00 pm. ..."

Reviewed on Aug 3, 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
The price is ￥16,776 per night from Aug 20 to Aug 21
￥16,776
￥22,188 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,482 reviews)
"Wonderful place to visit. It’s beautiful with lots to explore with the family!!!"

Reviewed on Aug 2, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,232 properties in Gloucester
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.

Discover the most popular places to visit in Gloucester

Rosewell Ruins

Learn about the local history of Gloucester when you spend time at Rosewell Ruins. Amble around this family-friendly area's picturesque gardens or attend a sporting event.

Rosewell Ruins

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals 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'd like to book a cheap Gloucester vacation package, consider planning a trip in January, February and April. You're likely to find lower prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Gloucester?
Typically, a handful of days is enough to check out the major attractions during your Gloucester vacation. However, if you want to have more time to kick back or take day tours, consider 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.
How to plan a trip to Gloucester?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Gloucester.
  2. Set your budget: Factor in costs like flights, transportation and food when calculating how much to save for your trip to Gloucester. Then, pick a property that fits your budget, whether that's an economical option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend exploring Gloucester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Gloucester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.