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

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.
  • A spacious lobby with a high ceiling, a central fireplace, and seating areas.
    Dec 17 - Dec 23

    Wingate by Wyndham Richmond Short Pump + Flight

    Short Pump
    6 nights
    3.0 star property
    8.4/10 - Very good (1,716 reviews)
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,330
    CA $1,059
    per traveller
    found 1 day ago
    Wingate by Wyndham Richmond Short Pump
  • The exterior of Omni Hotel with a modern design, featuring a large seating area with tables and chairs, and a variety of potted plants around the perimeter.
    Dec 17 - Dec 23

    Omni Richmond Hotel + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,592 reviews)
    "The staff was very accommodating and friendly. The location is wonderful. Close to some great dining and outdoor activities. The beds and pillows were extremely comfortable."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,668
    CA $1,429
    per traveller
    found 1 day ago
    Omni Richmond Hotel
  • A hallway with a grand chandelier, a wooden console table with a clock, and a mirrored wall reflecting an elevator.
    Dec 17 - Dec 23

    The Berkeley Richmond, Outset Collection by Hilton + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,323 reviews)
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,579
    CA $1,355
    per traveller
    found 1 day ago
    The Berkeley Richmond, Outset Collection by Hilton
  • A spacious living room with a large window, a modern chandelier, and a variety of framed artwork on the walls.
    Dec 17 - Dec 23

    The Commonwealth + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,416 reviews)
    "*"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,730
    CA $1,501
    per traveller
    found 1 day ago
    The Commonwealth
  • A multi-story hotel with outdoor seating areas and a well-maintained garden.
    Dec 17 - Dec 23

    Courtyard by Marriott Richmond Airport + Flight

    Sandston
    6 nights
    3.0 star property
    8.4/10 - Very good (1,002 reviews)
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,414
    CA $1,237
    per traveller
    found 1 day ago
    Courtyard by Marriott Richmond Airport

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.
See properties

Gloucester Hotel Deals

A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.

Hampton Inn Gloucester

Hampton Inn Gloucester
2.5 star property
1.8 km from Gloucester
9.2 out of 10, Wonderful, (812 reviews)
The price is CA $143
CA $159 total
includes taxes & fees
Nov 15 - Nov 16
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 $1,059 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.