Gloucester Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Gloucester

Holiday Inn Express Gloucester, an IHG Hotel
Holiday Inn Express Gloucester, an IHG Hotel
3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is S$136 per night from 23 Feb to 24 Feb
S$136
includes taxes & fees
23 Feb - 24 Feb
7.2/10 Good! (573 reviews)
Servicing room
"Only issue was no one bothered to service our room until day 4 out of five. At that point we were resting and said no thanks even though it needed servicing. Breakfast was delicious every morning and very well stocked."

Reviewed on 3 Jan,2025

Holiday Inn Express Gloucester, an IHG 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$171 per night from 26 Feb to 27 Feb
S$171
includes taxes & fees
26 Feb - 27 Feb
8.8/10 Excellent! (2,617 reviews)
Another awesome stay
"Hello, I have been to this resort before. It is an awesome place to stay. The check in process never takes no more than a few minutes. Jacob was very friendly and helpful. Nanu was also very helpful. He gave us a couple of coupons just in case we wanted to dine out. The unit itself was very clean. ..."

Reviewed on 16 Feb,2025

Hilton Vacation Club The Historic Powhatan 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 S$210 per night from 24 Feb to 25 Feb
S$210
includes taxes & fees
24 Feb - 25 Feb
8.8/10 Excellent! (1,227 reviews)
"Everything was fantastic"

Reviewed on 16 Feb,2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,075 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.