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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.
  • Reception
    Sept 6 - Sept 12

    Eagle Inn by Hotel O Richmond Midlothian Turnpike + Flight

    Midlothian
    6 nights
    2.5 star property
    6.0/10 - (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 June 11, 2026
    Roundtrip • Montreal (YUL) - Richmond (RIC)
    YUL - RIC • 1 stop RIC - YUL • 1 stop
    CA $1,012
    CA $868
    per traveller
    found 1 day ago
    Eagle Inn by Hotel O Richmond Midlothian Turnpike
  • Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
    Aug 30 - Sept 4

    Kingsmill Resort + Flight

    Kingsmill
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,009 reviews)
    "Although our stay was pretty good overall there needs to be some adjustments to the pet policy’s. Before I get into that, we had to call front desk to take care of a bug problem in the room. They came right away which I can appreciate. Moving on to our two dogs that came alone with us. We booked this resort off the strength that we can bring our dogs. Mind you we stayed three nights. On our last night, we were headed back after going to the outlets for the day. I received a phone call from Sarah..."
    Reviewed July 26, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - PHF • 1 stop PHF - YYZ • 1 stop
    CA $1,683
    CA $1,299
    per traveller
    found 9 hours ago
    Kingsmill Resort
  • Reception
    Sept 6 - Sept 12

    Turnpike Motel Richmond VA by Hotel O US 60 + Flight

    Midlothian
    6 nights
    2.5 star property
    6.4/10 - (97 reviews)
    "The stay went well no problems. I only seen one roach the tub in my room need to be repaired. The first night was a little noisy with the rooms next-door otherwise than that it was OK."
    Reviewed July 26, 2026
    Roundtrip • Montreal (YUL) - Richmond (RIC)
    YUL - RIC • 1 stop RIC - YUL • 1 stop
    CA $1,038
    CA $885
    per traveller
    found 1 day ago
    Turnpike Motel Richmond VA by Hotel O US 60
  • Exterior
    Aug 30 - Sept 4

    Kings Creek Plantation by TripForth + Flight

    Williamsburg
    5 nights
    3.5 star property
    8.6/10 - Excellent (43 reviews)
    "This is my second year here and I love it. It's perfectly clean, smells nice and feels homeh. I have a large family and there's always room for my kids to spread out and have their own space. I'll be back again."
    Reviewed July 13, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - PHF • 1 stop PHF - YYZ • 1 stop
    CA $1,896
    CA $1,647
    per traveller
    found 9 hours ago
    Kings Creek Plantation by TripForth
  • Property entrance
    Sept 4 - Sept 8

    The Commonwealth + Flight

    Downtown Richmond
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,375 reviews)
    "Very comfortable and spacious suite room and good central location."
    Reviewed July 26, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,120
    CA $982
    per traveller
    found 1 day ago
    The Commonwealth

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 $132
CA $146 total
includes taxes & fees
Aug 3 - Aug 4
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 $868 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.