Gloucester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,085
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,013 reviews)
The private beach is not very big. The marina is nice if you like boats. The pool was well maintained. However, there's no pool parking for the majority of people who go there for the river pool. So I didn't get to attend the main attraction. The restaurants are only open during short hours so plan a meal nearby. There are many unless you bring your own food. It was very clean and quiet. The soaps were refreshing. The complimentary robes mentioned were not there. I didn't stay very long but it was nice. Cool channels on the TV too. The employees were very helpful and kind.
Reviewed on Aug 20, 2026
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort
CA $1,031
per person
Nov 1 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (463 reviews)
Room was clean. Kitchen and laundry room were very nice. Kitchen had everything we needed to cook. Pull out couch was very comfortable
Reviewed on Aug 16, 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 $123
per night
Sep 20 - Sep 21
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $120
per night
Sep 20 - Sep 21
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $93
per night
Sep 20 - Sep 21
9.2/10 Wonderful! (3,793 reviews)
"What a cluster. It took over an hour just to check in…,then after waiting they had the audacity to offer a “welcome” gift that was nothing more than trying to sell themselves. They should have had everyone working to check people in….not try to sell themselves. Very unprofessional and annoying."
Reviewed on Aug 19, 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.
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.
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.
Rosewell Ruins
6.0/10 (2 reviews)
Learn about the local history of Gloucester when you spend time at Rosewell Ruins. 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.
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 $924 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.
