Skip to main content
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 sitting area
    Sept 14 - Sept 18

    Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel + Flight

    Colonial Williamsburg
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,880 reviews)
    "If you're going to Colonial Williamsburg, it would be hard to find a more conveniently located hotel. The rooms are nice, and it's great that it has multiple things to do, including mini golf. The only thing keeping it from a five stars is that the beds were not comfortable. Maybe they'd work better for someone else, but neither I or the person I travelled with slept very well because of it. Still, the fact that you can walk to Colonial Williamsburg made it worth it for us!"
    Reviewed August 5, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $999
    CA $890
    per traveller
    found 1 day ago
    Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
  • BBQ/picnic area
    Sept 25 - Sept 30

    Vaiden Inn + Flight

    New Kent
    5 nights
    3.5 star property
    10/10 - Exceptional (21 reviews)
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,436
    CA $1,157
    per traveller
    found 1 day ago
    Vaiden Inn
  • Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
    Sept 21 - Sept 25

    Kingsmill Resort + Flight

    Kingsmill
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,015 reviews)
    "Great services, views, and perfect for a small getaway"
    Reviewed August 4, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,287
    CA $1,057
    per traveller
    found 23 hours ago
    Kingsmill Resort
  • Property entrance
    Oct 17 - Oct 21

    The Commonwealth + Flight

    Downtown Richmond
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,373 reviews)
    "The Commonwealth is our "go to" hotel when we stay in Richmond, Virginia, primarily because the rooms are huge and a great value, and the staff is friendly, helpful and determined. I do have to mention, though, that I would hope the hotel would hire more staff members. It appears that the staff on hand are expected to serve many roles, which causes the service to lag. For instance, when we checked in this last time, there was no one at the reception desk and the housekeeping supervisor..."
    Reviewed August 4, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,309
    CA $1,131
    per traveller
    found 1 day ago
    The Commonwealth
  • Deluxe Studio Suite, 1 King Bed, Non Smoking
    Sept 25 - Sept 30

    La Quinta Inn by Wyndham Richmond South + Flight

    Bellwood
    5 nights
    3.0 star property
    7.2/10 - Good (1,001 reviews)
    "O"
    Reviewed August 4, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,147
    CA $1,003
    per traveller
    found 1 day ago
    La Quinta Inn by Wyndham Richmond South

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

Restaurant

Hampton Inn Gloucester

Hampton Inn Gloucester
2.5 star property
1.8 km from Gloucester
9.2 out of 10, Wonderful, (788 reviews)
The price is CA $146
CA $162 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn 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.
See all properties in Gloucester

Frequently Asked Questions

How much does a Gloucester vacation package cost?

You'll find cheap prices from CA $890 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.