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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was CA $1,089, price is now CA $944 per person
CA $944
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,144 reviews)
The 2 room suite was bigger and better than expected. The room was clean and comfortable. Ample parking. The staff were friendly. The kitchenette was well stocked with anything you could need. Beds were comfortable. The fireplace was a nice addition. Highly recommend. Would definitely stay again

Reviewed on Nov 2, 2026

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was CA $1,144, price is now CA $956 per person
CA $956
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (2,999 reviews)

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,774, price is now CA $1,489 per person
CA $1,489
per person
Dec 28 - Jan 3
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Safe. Clean. Quiet. Beautiful surroundings and property. However, the rooms are out dated/old.

Reviewed on Nov 2, 2026

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was CA $1,421, price is now CA $1,257 per person
CA $1,257
per person
Dec 28 - Jan 3
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (413 reviews)
We arrived later in the evening and after we found the sheets, blanket and pillows for the pullout bed, we were able to put them on. After putting them on, we noticed what appeared to be bed bugs in the sheets. We informed the front office and they placed in a different room, but no reimbursement for the trouble. When we checked in, we were told that we would need to return the next morning to pick up the required parking passes, which would put us at risk of being towed (both vehicles). Fortunately we weren’t towed. When we went to get the passes the next morning, we weren’t towed asked how things were so far. We mentioned the bed bugs situation and the woman across the room from the main check in said that it wasn’t bed bugs and that it was ink. We saw what we saw and we’ve stayed at a number of hotels due to our daughter being a competitive swimmer and that often requires us to travel and stay in hotels.

Reviewed on Nov 2, 2026

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

2.5 out of 5
Price was CA $1,324, price is now CA $1,211 per person
CA $1,211
per person
Dec 28 - Jan 3
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,311 reviews)

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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.
See properties

Frequently asked questions

How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $944 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?

  1. Pick your travel dates: What you plan to do in Gloucester and your preferred season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.