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 $1,762
per person
Nov 8 - Nov 15
found 22 hours ago
Roundtrip flight included
Halifax (YHZ) to Richmond (RIC)
8.6/10 Excellent! (1,007 reviews)
We arrived at 10.15 pm due to car problems. Tried to call them to advise of our lateness but all numbers went through to a call centre who did not answer. Everything was closed so there was no food or drink available and the receptionist was unhelpful. There wasn't even bottled water in our room. Vending machines were shown on the map provided but only ice machines were available. Very little information provided about the amenities. Our windows were filthy and there was mould around the basin tap. Squeaky floorboards. Beautiful grounds and views of the river. Overall, very disappointing - a hotel that promises a lot but does not deliver.
Reviewed on Sep 8, 2026
Rochambeau Roadside Inn
CA $1,579
per person
Oct 23 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
10/10 Exceptional! (33 reviews)
What a hidden gem! I’ll admit we were a little skeptical when we saw how great all the reviews were, but this place totally deserves it! It’s nothing like those typical chain hotels, so don’t expect a big lobby with old carpets and a subpar breakfast buffet. This place is for people who want cleanliness and a place that thought of all the little things! First and foremost…SO CLEAN! The room smells nice when you enter. Beds are soft. A proper amount of towels (no calling down for extras). A nice modern tile shower with incredible water pressure. Outlets everywhere. Free WiFi. An ice house with (ice, obviously) with free bike rentals and a little closet with all the stuff you might need but forgot. What a great place!!
Reviewed on Aug 31, 2026
Ready to book your vacation to Gloucester?
Gloucester Hotel Deals
Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
CA $137
CA $152 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (794 reviews)
"Property met standards for Hampton Inn."
Reviewed on Sep 1, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $118
CA $150 total
Sep 29 - Sep 30
includes taxes & fees
8.8/10 Excellent! (2,868 reviews)
"The property is clean and very nice. It’s a little dated. The technology (tvs) need to be updated so the guests can stream. That would be my only complaint."
Reviewed on Sep 8, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $93
CA $145 total
Sep 9 - Sep 10
includes taxes & fees
9.2/10 Wonderful! (3,830 reviews)
"One of the best places I’ve stayed."
Reviewed on Sep 8, 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.
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.
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.
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.
Frequently asked questions
How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $908 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.
