Gloucester Vacations

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Find the Best Gloucester Vacation Packages

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
The price is ₩152,123 per night from Jun 24 to Jun 25
₩152,123
₩169,313 total
Jun 24 - Jun 25
includes taxes & fees
7.2/10 Good! (611 reviews)
"The staff was excellent. Michael was an excellent help look as mob oh re s"

Reviewed on Jun 10, 2025

Holiday Inn Express Gloucester by IHG
Vacation Village At Williamsburg
Vacation Village At Williamsburg
3 out of 5
4870 Longhill Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,438 reviews)
"Property was great. Guest services was bad. Requested extra blankets and never received them."

Reviewed on Jun 21, 2025

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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
Fully refundableReserve now, pay when you stay
The price is ₩146,778 per night from Jun 24 to Jun 25
₩146,778
₩195,982 total
Jun 24 - Jun 25
includes taxes & fees
8.8/10 Excellent! (1,386 reviews)
"Great place to stay, close to everything in Williamsburg"

Reviewed on Jun 21, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,208 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.

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.