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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was CA $1,327, price is now CA $1,056 per person
CA $1,056
per person
Nov 28 - Dec 4
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very good! (1,715 reviews)
AC in first room assigned was broken, beds were too high for my wife to get in. Chipped Sheetrock throughout. Main lobby was horrible and the dining area was unusable. Hotel was in lousy location.

Reviewed on Oct 28, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $2,637, price is now CA $1,860 per person
CA $1,860
per person
Nov 28 - Dec 5
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Price was CA $2,360, price is now CA $1,982 per person
CA $1,982
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.8/10 Exceptional! (415 reviews)

The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was CA $1,349, price is now CA $1,188 per person
CA $1,188
per person
Nov 28 - Dec 4
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,330 reviews)
The staff was friendly and professional. Room was clean everything worked and very clean. I enjoyed staying here. I will be back the next time I am in Richmond.

Reviewed on Oct 28, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,403, price is now CA $1,249 per person
CA $1,249
per person
Dec 19 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)

Ready to book your vacation to Gloucester?

 

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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 $136 per night from Nov 4 to Nov 5
CA $136
CA $152 total
Nov 4 - Nov 5
includes taxes & fees
9.2/10 Wonderful! (807 reviews)
"Staff is great. Rooms are clean. Love having liquid soap and lotion next to the sink. Also 4 towel hooks in the bathroom."

Reviewed on Oct 24, 2026

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! (4,011 reviews)
"Our unit was very clean and spacious, we enjoyed our stay."

Reviewed on Oct 28, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,293 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.
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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 $1,056 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.