Gloucester Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Gloucester

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 2.425.672 ₫ per night from 27 Aug to 28 Aug
2.425.672 ₫
3.064.111 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8.8/10 Excellent! (2,662 reviews)
"Love it! this place had more then what I expected .great place to go if you need at little get away from the world and take a mental break from the world. it would have been nice to have activities going on in this place. it’s more like a resort then place to stay like a motel or hotel"

Reviewed on 27 Jul 2026

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 2.273.585 ₫ per night from 3 Aug to 4 Aug
2.273.585 ₫
3.207.657 ₫ total
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,864 reviews)
"Overall easy stay for one night. Breakfast was very basic. Pool was fun for the kids."

Reviewed on 28 Jul 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
The price is 2.438.085 ₫ per night from 17 Aug to 18 Aug
2.438.085 ₫
3.520.105 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (3,680 reviews)
"This was a small family/friends getaway that was much needed the resort accommodated all our needs and we had a wonderful time!"

Reviewed on 28 Jul 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,189 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.

Stay near popular Gloucester attractions

Beaverdam Park

Explore Beaverdam Park's 635-acre reservoir through hiking trails and tranquil waterways. Rent a boat to fish for largemouth bass or observe diverse wildlife from the park's scenic overlooks.
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Frequently asked questions

How much does a Gloucester holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday 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 travellers 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 holiday. 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 holiday as a package?
You can enjoy significant savings on your Gloucester retreat by booking a customised holiday package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Gloucester?
If you're considering a spontaneous Gloucester holiday, 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 accommodation and airfare: After you've nailed down your trip dates and duration, book the right Gloucester holiday package for you.