Gloucester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was CA $1,307, price is now CA $1,149 per person
CA $1,149
per person
Dec 19 - Dec 24
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (413 reviews)

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,849, price is now CA $1,547 per person
CA $1,547
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,448, price is now CA $1,276 per person
CA $1,276
per person
Dec 19 - Dec 24
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (328 reviews)
I really enjoyed this cottage! It was very nice with plenty of space. I stayed in the off season so the price was excellent. Far better than a hotel room. I will definitely stay here again.

Reviewed on Oct 27, 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 $1,492, price is now CA $1,336 per person
CA $1,336
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
9.2/10 Wonderful! (1,311 reviews)

Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
Price was CA $1,355, price is now CA $1,265 per person
CA $1,265
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
5.4/10 (3 reviews)

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Gloucester Hotel Deals

Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 9 to Nov 10
CA $135
CA $151 total
Nov 9 - Nov 10
includes taxes & fees
Hampton Inn Gloucester
Perfect for long-term workers & short stays—comfort, style & convenience await!

Perfect for long-term workers & short stays—comfort, style & convenience await!

Gloucester VA
8.2/10 Very good! (25 reviews)
"Host was super helpful. Everything we needed was provided.We would stay again."

Reviewed on Oct 10, 2026

Get rates
Perfect for long-term workers & short stays—comfort, style & convenience await!
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Nov 5 to Nov 6
CA $94
CA $147 total
Nov 5 - Nov 6
includes taxes & fees
9.2/10 Wonderful! (4,014 reviews)
"We were pleasantly surprised by our spacious and clean condo style room. The property is lovely and well maintained. Very secure and good location for attractions."

Reviewed on Oct 30, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,244 properties in Gloucester
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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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 $1,149 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.