Gloucester Trips (flight + hotel)

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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
8.6/10 Excellent! (1,431 reviews)
"It was very busy during check in but the staff did a great job. The room was very large and clean. The pillows were small but the beds were very comfortable. The room itself was further from the pool than expected and the pool was pretty crowded so we didn't bother with it. The location is good- ..."

Reviewed on Jun 20, 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 P6,123 per night from Jun 24 to Jun 25
P6,123
P8,175 total
Jun 24 - Jun 25
includes taxes & fees
8.8/10 Excellent! (1,392 reviews)
"Part of historic Williamsburg, lovely old property with all the amenities."

Reviewed on Jun 23, 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 P4,211 per night from Jun 30 to Jul 1
P4,211
P4,831 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
"The stay was Nice. Guest Rooms were VERY spacious and comfortable. Only con is the Bugs especially with it being the summer time. Overall stay was Nice and staff was friendly. Shout out to Tony for the delightful service at Williamsburg Colonial location."

Reviewed on Jun 22, 2025

Westgate Historic Williamsburg Resort
See all 2,227 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 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 many days is enough for Gloucester?
Typically, a handful of days is enough to check out the major attractions during your Gloucester vacation. 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 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.

Popular places to visit

Ware Parish Church

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

Ware Parish Church

Walter Reed Birthplace

You can spend time browsing the exhibits at Walter Reed Birthplace during your travels in Gloucester. Experience the festivals and art scene in this family-friendly area.

Walter Reed Birthplace
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.