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A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

Gloucester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Gloucester vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Golf
    Aug 26 - Aug 30

    Griffin Hotel, an official Colonial Williamsburg Hotel + Flight

    Colonial Williamsburg
    4 nights
    3.0 star property
    8.8/10 - Excellent (844 reviews)
    "I was charged $32.10 and $14.98 on my credit card with no explanation. I messaged via the Expedia inbox/chat feature to try and get an explanation, but got no response. Terrible experience."
    Reviewed July 24, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,349
    CA $1,090
    per traveller
    found 1 day ago
    Griffin Hotel, an official Colonial Williamsburg Hotel
  • Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
    Aug 26 - Aug 30

    The Colonies at Williamsburg + Flight

    Williamsburg
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,012 reviews)
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,354
    CA $1,104
    per traveller
    found 1 day ago
    The Colonies at Williamsburg
  • Property entrance
    Sept 6 - Sept 11

    The Commonwealth + Flight

    Downtown Richmond
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,373 reviews)
    "Historic is one way to describe it... dated another. The rooms are dark, dreary. The property is hard to access due to surrounding construction which furthers the issues. I was invaded by Security as I had just stepped out of the shower and was in the bedroom and I heard the door open. I called out and then frantically threw some clothes on to find a man standing in the door saying "Is the shower leaking as the room downstairs called to say they had a leak". It was 4 in the afternoon. I had..."
    Reviewed July 24, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,329
    CA $1,096
    per traveller
    found 1 day ago
    The Commonwealth
  • Property amenity
    Oct 15 - Oct 18

    Wedmore Place + Flight

    Williamsburg
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Place was beautiful and historic. Nice grounds, walkable to winery and restaurant. Nice breakfast. Had to rely on front desk for ice. No fridge in room. Microwave was downstairs. Rooms were not well insulated for sound. Could hear loud occupants in adjacent room late at night."
    Reviewed July 19, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,313
    CA $1,098
    per traveller
    found 22 hours ago
    Wedmore Place
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sept 6 - Sept 11

    The Berkeley Richmond, Outset Collection by Hilton + Flight

    Downtown Richmond
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,382 reviews)
    "Nice place!"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,407
    CA $1,198
    per traveller
    found 1 day ago
    The Berkeley Richmond, Outset Collection by Hilton

Discover the most popular places to visit in Gloucester

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.

Gloucester Hotel Deals

Exterior

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG
3.5 star property
1.7 km from Gloucester
7.2 out of 10, Good, (717 reviews)
"Breakfast was good"
The price is CA $131
CA $146 total
includes taxes & fees
Aug 5 - Aug 6
Holiday Inn Express Gloucester by IHG
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.
See all properties in Gloucester

Frequently Asked Questions

How much does a Gloucester vacation package cost?

You'll find cheap prices from CA $1,090 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.