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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.
  • Lobby
    Sept 26 - Sept 29

    Travelodge by Wyndham Williamsburg Colonial Area + Flight

    Williamsburg
    3 nights
    2.0 star property
    6.8/10 - (1,000 reviews)
    "The room was clean, AC worked great, staff was friendly, and the hotel location is top notch a short drive to Colonial Williamsburg, in fact with in walking distance, if you don’t mind the exercise, and a short drive to Busch Gardens. The only issue we had was that we were on the top floor on the far end of the hotel and there’s only one elevator and it was on the other end."
    Reviewed July 7, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $684
    CA $649
    per traveller
    found 1 day ago
    Travelodge by Wyndham Williamsburg Colonial Area
  • Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
    Sept 26 - Sept 29

    Kingsmill Resort + Flight

    Kingsmill
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "Check in was delayed due to the room not being ready by 4 pm. The gentleman that checked us in was very nice and provided complimentary breakfast to all in our party. Beautiful grounds, we loved the lazy river and bar."
    Reviewed July 29, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,096
    CA $944
    per traveller
    found 1 day ago
    Kingsmill Resort
  • Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
    Sept 26 - Sept 29

    King’s Creek Resort by Spinnaker + Flight

    Williamsburg
    3 nights
    4.5 star property
    8.8/10 - Excellent (225 reviews)
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $792
    CA $723
    per traveller
    found 1 day ago
    King’s Creek Resort by Spinnaker
  • Premium bedding, in-room safe, desk, laptop workspace
    Sept 26 - Sept 29

    Days Inn & Suites by Wyndham Williamsburg Colonial + Flight

    Williamsburg
    3 nights
    2.5 star property
    6.2/10 - (1,000 reviews)
    "You got nice rooms and ghetto rooms. Don’t know what you’re gonna get."
    Reviewed July 28, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $736
    CA $701
    per traveller
    found 1 day ago
    Days Inn & Suites by Wyndham Williamsburg Colonial
  • Exterior
    Sept 26 - Sept 29

    Warner Hall + Flight

    Gloucester
    3 nights
    3.0 star property
    10/10 - Exceptional (34 reviews)
    "From the immaculate grounds, to the unreal US history from the Warner family, this destination is a true gem. Phil and Laura; the inn keepers hosted our amazing stay and provided information on the rich history of the site. Austin’s is a wonderful high quality dining establishment on premises with outstanding cuisine, quiet atmosphere, and wonderful wine recommendations by Christian; a top-notch waiter and sommelier. The original house was remodeled to provide outstanding comfort and..."
    Reviewed July 7, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,188
    CA $1,139
    per traveller
    found 1 day ago
    Warner Hall

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, (720 reviews)
"The desk staff was amazing and very helpful. Room was, meh. Everything felt damp.. floor, sheets, pillows. Everything. We did not use the pool or gym but did have breakfast. It was what you expect with a continental breakfast. Disappointed that the pancake machine was out of order but these things happen."
The price is CA $127
CA $141 total
includes taxes & fees
Aug 2 - Aug 3
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 $649 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.