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 SAR 401 per night from May 4 to May 5
SAR 401
SAR 447 total
includes taxes & fees
4 May - 5 May
7.2/10 Good! (591 reviews)
"What you would normally get at Holiday Inn"

Reviewed on 29 March 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
The price is SAR 289 per night from Apr 21 to Apr 22
SAR 289
SAR 436 total
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (2,682 reviews)
"The property was clean, family friendly with great amenities for the kids like indoor pool, and mini golf. We are planning to go back in the Summer to enjoy the outdoor pool as well!"

Reviewed on 16 April 2025

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
The price is SAR 409 per night from May 2 to May 3
SAR 409
SAR 508 total
includes taxes & fees
2 May - 3 May
8.6/10 Excellent! (1,226 reviews)
"We loved the sports courts and the indoor pool. The property was nice and clean and well lit. The condo itself was super clean and seemed like new coats of paint and new flooring. The beds were comfortable and accommodated our family of 5 nicely. The kitchen was well stocked with pots/pans/bowls ..."

Reviewed on 18 April 2025

Vacation Village At Williamsburg
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 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.

Discover the most popular places to visit in Gloucester