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.
Eagle Inn by Hotel O Richmond Midlothian Turnpike

Eagle Inn by Hotel O Richmond Midlothian Turnpike

2.5 out of 5
Midlothian
Price was CA $775, price is now CA $706 per person
CA $706
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6/10 (24 reviews)
Booked room thru Expedia. Expedia charged my card $158. Get to hotel. They say room is booked but they only received $38. They said I have to pay the balance. I left. Still awaiting refund.

Reviewed on Jun 11, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,047, price is now CA $919 per person
CA $919
per person
Sep 10 - Sep 14
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,790 reviews)
ty

Reviewed on Jul 9, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,136, price is now CA $1,002 per person
CA $1,002
per person
Aug 20 - Aug 24
found 15 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
Hotel was a bit run down, elevators had noticeable scratches Toile Toilet not clean Not staying here again

Reviewed on Jul 8, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,409, price is now CA $1,244 per person
CA $1,244
per person
Sep 10 - Sep 14
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
Beautiful! Lots to do with chidren.

Reviewed on Jul 8, 2026

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
Price was CA $905, price is now CA $815 per person
CA $815
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,003 reviews)
Clean

Reviewed on Jul 9, 2026

Ready to book your vacation to Gloucester?

 

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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $132 per night from Aug 3 to Aug 4
CA $132
CA $147 total
Aug 3 - Aug 4
includes taxes & fees
7.2/10 Good! (713 reviews)
"My room smelled of mold and mildew.. My bedding felt damp. Staff quickly exchanged linens, but next night, those linens felt damp also. Room smelled moldy the entire trip. Other then that it was fair."

Reviewed on Jul 6, 2026

Holiday Inn Express Gloucester by IHG
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 6 to Aug 7
CA $150
CA $186 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (2,597 reviews)
"Very clean and loved the pool."

Reviewed on Jul 9, 2026

Vacation Village At Williamsburg
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 $131 per night from Jul 21 to Jul 22
CA $131
CA $190 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (3,598 reviews)
"Beautiful property in close proximity to Colonial Williamsburg for the 250th Celebration. The room was excellent, except for the smoke detector battery being outdated. The battery chirped incessantly at 3am. Had to get Security to remove it in the middle of the night. Pools were very nice."

Reviewed on Jul 9, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,095 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 $706 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.