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
8.6/10 Excellent! (1,452 reviews)
"I like the layout of the property being similar to townhouses. It was a busy weekend but the service staff was attentive and keep the whole area clean."

Reviewed on 23 Jun 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
The price is 2.798.630 ₫ per night from 1 Jul to 2 Jul
2.798.630 ₫
3.736.787 ₫ total
1 Jul - 2 Jul
includes taxes & fees
8.8/10 Excellent! (1,392 reviews)
"Part of historic Williamsburg, lovely old property with all the amenities."

Reviewed on 23 Jun 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Westgate Historic Williamsburg Resort
Westgate Historic Williamsburg Resort
3.5 out of 5
1324 Richmond Road, Williamsburg, VA
The price is 1.924.940 ₫ per night from 7 Jul to 8 Jul
1.924.940 ₫
2.208.195 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Was very nice."

Reviewed on 20 Jun 2025

Westgate Historic Williamsburg Resort
See all 2,225 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 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.

Popular places to visit

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

Gloucester Museum of History

You can study the exhibits at Gloucester Museum of History, a museum with a storied past, during your trip to Zanoni. Experience the festivals and art scene in this family-friendly area.

Gloucester Museum of History

Ware Parish Church

You can find out about the history of Gloucester with a trip to Ware Parish Church. Experience the festivals and art scene in this family-friendly area.

Ware Parish Church