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.
The Colonies at Williamsburg
CA $1,101
per person
Oct 2 - Oct 9
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
9/10 Wonderful! (1,026 reviews)
The location was great for our trip to Busch Gardens. The rooms were spacious and clean, the employees courteous and helpful. While we didn’t use the amenities to include the pool and the hot tub, they seemed well kept and clean.
Reviewed on Aug 25, 2026
Wedmore Place
CA $1,617
per person
Oct 2 - Oct 9
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
9.4/10 Exceptional! (1,001 reviews)
Wedmore Place was an awesome place to stay. It gave you the sense of staying in a historic castle or inn. The grounds were lovely and felt removed and quiet. There was a great sense of peace here. Walking distance from the winery for a tasting and a tavern for a great elevated dining experience. Overall a great place.
For people who like very hot showers or strong water pressure, my room did not have that. It wasn't bad for me but I know people like it more intense than me.
Also, the thermostat was just kind of odd/confusing, but once we figured it out we were comfortable. Oh, and if you need air movement/noise, bring a fan.
The bed was awesome. The atmosphere of the building was awesome. The breakfast was awesome.
I would definitely stay here again.
Reviewed on Aug 23, 2026
Kingsmill Resort
Kingsmill
CA $1,373
per person
Oct 2 - Oct 9
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,011 reviews)
This place is super gorgeous and fun, but it does need some upgrades. The condo we stayed in was very small (double beds) and we could hear both the dog and the conversation in the next room over. It didn't really feel private, and the dog was super annoying because it barked or whined extensively during the day and at night. I called/texted the concierge, but they wanted me to figure out which room it was instead of looking on their own map. I complied, but it wasn't easy for me to figure out which condo it was because the layout was odd. The concierge was polite, but he didn't seem to care that this was affecting our stay. (If a Pro Golfer were staying there and complained about noise, I'm pretty sure they wouldn't ask them to check the property and figure it out.) Things like ice and beverages weren't easily accessible due to the condo layout. The lobby was beautiful, but the shop inside was closed by 9pm. The rooms need new carpet and upgrading and the mattresses felt cheap. The pools and gym were all amazing.
Reviewed on Aug 25, 2026
Holiday Inn Club Vacations Williamsburg Resort by IHG
CA $1,352
per person
Oct 2 - Oct 9
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
9/10 Wonderful! (591 reviews)
The room was super clean and the staff was super friendly I definitely would stay here again.
Reviewed on Aug 11, 2026
Ready to book your vacation to Gloucester?
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
CA $127
CA $142 total
Sep 24 - Sep 25
includes taxes & fees
7.2/10 Good! (732 reviews)
"The staff that ran the breakfast were so nice and so helpful. I missed breakfast by 10 minutes and needed milk so she brought me some even though the “kitchen” area was closed."
Reviewed on Aug 24, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $121
CA $153 total
Sep 17 - Sep 18
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
CA $93
CA $146 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (3,827 reviews)
"We have been staying here several times a year for the past 15+ years. The grounds are beautiful and well maintained and the units are very clean and comfortable; however while we’ve always enjoyed the pool for adults only this time it no longer is enforced. We had to dodge people throwing a football, ..."
Reviewed on Aug 26, 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.
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.
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.
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.
Frequently asked questions
How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $1,101 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.
