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.
Kingsmill Resort
Kingsmill
CA $1,212
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
8.8/10 Excellent! (1,028 reviews)
The amenities were excellent. Staff were very nice. My only complaint was the accumulation. We opted for a condo over a hotel room since it was a special occasion. It appears we were put in an animal friendly condo as we were surrounded by people with dogs, and the furnishings inside were old. The sliding glass door didn’t lock, the WiFi didn’t work in the bedroom, the television remote didn’t work, and the bedroom was warm as the A/C vent was small and didn’t cool the room. Given the price that we paid, it was very disappointing.
Reviewed on Sep 3, 2026
The Commonwealth
Downtown Richmond
CA $1,934
per person
Oct 17 - Oct 24
found 23 hours ago
Roundtrip flight included
Halifax (YHZ) to Richmond (RIC)
8.8/10 Excellent! (1,401 reviews)
The place looks a lot better in the pictures than in reality. I was not impressed that they charge me to check in an hour early when there were rooms available. Every time I approached the front desk I had to wait for someone to come up, which was not long, but jut was not the normal hospitality experience you normally experience elsewhere.
Reviewed on Sep 2, 2026
Ready to book your vacation to Gloucester?
Gloucester Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $118
CA $150 total
Sep 21 - Sep 22
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $93
CA $146 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (3,791 reviews)
"It was a wonderful trip!!!!!"
Reviewed on Sep 2, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $104
CA $151 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,944 reviews)
"It is worth staying here if you are going to Colonial Williamsburg. The hotel parking lot is essentially the visitors' center parking lot, and the hotel gives you a pass to park for free. They also give you a coupon for a discount on tickets to Colonial Williamsburg. I loved the huge (Olympic-sized?) ..."
Reviewed on Sep 3, 2026
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
Beaverdam Park
Explore the great outdoors at Beaverdam Park, a lovely green space in Gloucester. Experience the festivals and art scene in this family-friendly area.
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.
Rosewell Ruin and Visitor Center
6.0/10 (2 reviews)
Learn about the local history of Gloucester when you spend time at Rosewell Ruin and Visitor Center. Amble around this family-friendly area's picturesque gardens or attend a sporting event.
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.
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.
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.
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.
Ark Park
Ark 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.
Frequently asked questions
How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $990 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.