Gloucester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Gloucester

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 S$169 per night from 27 Jul to 28 Jul
S$169
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (698 reviews)
"Our service and staff were exceptional. Breakfast service very nice with a wide variety of food options (missed my bacon!!). For this elderly lady it would have been nice to have a more convent/accessible make-up mirror. Thank you"

Reviewed on 13 Jul, 2025

Hampton Inn Gloucester
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
8.8/10 Excellent! (1,434 reviews)
"Wonderful property within walking distance of Colonial Williamsburg. Easy parking and discount on tickets."

Reviewed on 14 Jul, 2025

Get rates
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
Fully refundableReserve now, pay when you stay
The price is S$159 per night from 12 Aug to 13 Aug
S$159
12 Aug - 13 Aug
includes taxes & fees
8.8/10 Excellent! (2,844 reviews)
"Very clean and staff was courteous. Lawns were nicely trimmed."

Reviewed on 12 Jul, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,253 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.