Gloucester Vacation Packages
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Your Gloucester Vacation
From its coastal scenery to its rich history and beyond, there's loads to like about Gloucester. Discover the wonders of this captivating city with a Gloucester vacation package that's made for you. Eager to do a bit of sightseeing? A trip to Gloucester isn't complete without checking out Middle Peninsula State Park, Gloucester Museum of History and other major attractions. Your Gloucester vacation is clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
Top Gloucester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort
CA $1,118
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.4/10 Exceptional! (396 reviews)
Lovely, clean spacious apartment. Close proximity to Busch gardens and Colonial Williamsburg
Reviewed on Sep 28, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
CA $1,327
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,974 reviews)
The Woodlands Hotel is a great place to stay...close the the visitors center. Breakfast was well maintained and as far as coffee goes at hotels, this was pretty good. I recommend staying at the Woodlands Hotel when you come to Colonial Williamsburg
Reviewed on Sep 30, 2026
Ready to book your vacation to Gloucester?
Gloucester Hotel Deals
Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
CA $150
CA $167 total
Oct 15 - Oct 16
includes taxes & fees
Warner Hall
4750 Warner Hall Road Gloucester VA
CA $296
CA $329 total
Oct 28 - Oct 29
includes taxes & fees
10/10 Exceptional! (43 reviews)
"The historical significance of this property is reason alone to visit. George Washington's great grandfather established a plantation there in 1642. While original buildings were burned, the owners have restored according to drawings and records. There's a cemetery on property with graves from 1600s. ..."
Reviewed on Sep 19, 2026
Perfect for long-term workers & short stays—comfort, style & convenience await!
Gloucester VA
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
Middle Peninsula State Park
10.0/10 (1 review)
You can take time to visit Middle Peninsula State Park during your travels to Gloucester. Experience the festivals and art scene in this family-friendly area.
Shoppes at Gloucester
You can do some window-shopping at Shoppes at Gloucester during your trip to Gloucester. Experience the festivals and art scene in this family-friendly area.
Purtan Island
Commune with nature and explore the great outdoors at Purtan Island during your travels in Gloucester. Experience the festivals and art scene in this family-friendly area.
Thousand Trails Beach Park
Thousand Trails Beach Park is just one of the places to see in Gloucester, so why not enjoy the other things to explore during your travels? Experience the festivals and art scene in this family-friendly area.
Main Street Center
You can do some window-shopping at Main Street Center during your stay in Gloucester. Experience the festivals and art scene in this family-friendly area.
Gloucester Golf Club
Enjoy a round of golf in Gloucester at Gloucester Golf Club. Experience the festivals and art scene in this family-friendly area.
Gloucester Museum of History
9.0/10 (4 reviews)
You can study the exhibits at Gloucester Museum of History, a museum with a storied past, during your trip to Gloucester. Experience the festivals and art scene in this family-friendly area.
Gloucester Public Library
Gloucester Public Library is just one of the places to see in Gloucester, so why not enjoy the other things to explore during your travels? Experience the festivals and art scene in this family-friendly area.
Frequently asked questions
How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $1,118 on Expedia for your Gloucester break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Gloucester costs.
What are the cheapest months to go to Gloucester?
You can generally find reduced prices and better availability in January, February and April. Take a look at our cheap Gloucester vacation packages and you could get some excellent off-season deals.
How many days is enough for Gloucester?
The ideal length of your Gloucester vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the leading sights and explore some hidden gems along the way.
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 a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Gloucester package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gloucester adventure underway.
Is it cheaper to book a Gloucester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your Gloucester trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Gloucester?
Score amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Gloucester escape.
How to plan a trip to Gloucester?
- Pick your travel dates: What you plan to do in Gloucester and your preferred season will help you decide when to get away.
- Set your budget: Factor in expenses like flights, meals and transportation when working out how much to set aside for your trip to Gloucester. Then, pick a hotel that matches your budget, whether that's an economical option or a deluxe getaway.
- Decide how many days away: Start by making a list of all the attractions you'd like to get to in Gloucester. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Gloucester vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
