A street with historic buildings, cars, and a cyclist.

Southwestern Ontario Holidays from AU$1,588

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 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 Southwestern Ontario Holiday

When wanderlust beckons, answer it with a holiday package to Southwestern Ontario. Get set to enjoy nature, culture, history, and more in this exciting destination. A trip to Southwestern Ontario wouldn't be complete without getting to some of its leading cities, starting with Hamilton. Some of the top attractions here include Tim Hortons Field and Village Theatre Waterdown. Windsor is another favourite with Southwestern Ontario travellers. Visitors to this exciting city enjoy Detroit Windsor Tunnel and Caesars Casino. Expedia is a one-stop shop when it comes to planning your Southwestern Ontario holiday. From flights and accommodation, to rental cars and activities, we know how to curate a travel experience like no other.

The Latest Southwestern Ontario Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 21 Dec - 25 Dec

    Montecassino Hotel and Event Venue + Flight

    North York
    4 nights
    3.0 star property
    7.6/10 - Good (1,164 reviews)
    Return • Istanbul (IST) - Toronto (YYZ)
    IST - YYZ • Direct YYZ - IST • 1 stop
    AU$1,761
    AU$1,588
    per traveller
    found 19 hours ago
    Montecassino Hotel and Event Venue
  • 21 Dec - 25 Dec

    Modern Apartments in North York + Flight

    North York
    4 nights
    4.0 star property
    8.0/10 - Very good (407 reviews)
    Return • Istanbul (IST) - Toronto (YYZ)
    IST - YYZ • Direct YYZ - IST • 1 stop
    AU$2,294
    AU$1,960
    per traveller
    found 19 hours ago
    Modern Apartments in North York
  • 21 Dec - 25 Dec

    Willowdale Hotel Toronto North York + Flight

    North York
    4 nights
    3.0 star property
    8.4/10 - Very good (815 reviews)
    "The location to sunnybrook hotel is approx 15 minutes away. It is also close to the 401. Very quiet area of town. The hotel was clean, quiet and comfortable. Staff were very friendly. Will definitely return to this hotel."
    Reviewed October 29, 2026
    Return • Istanbul (IST) - Toronto (YYZ)
    IST - YYZ • Direct YYZ - IST • 1 stop
    AU$1,954
    AU$1,728
    per traveller
    found 19 hours ago
    Willowdale Hotel Toronto North York
  • 21 Dec - 25 Dec

    Hilton Toronto/Markham Suites Conference Centre & Spa + Flight

    Markham
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,770 reviews)
    "great location, perfect for a weekend staycation"
    Reviewed November 3, 2026
    Return • Istanbul (IST) - Toronto (YYZ)
    IST - YYZ • Direct YYZ - IST • 1 stop
    AU$1,797
    AU$1,611
    per traveller
    found 19 hours ago
    Hilton Toronto/Markham Suites Conference Centre & Spa
  • 21 Dec - 25 Dec

    Liberty Suites Hotel + Flight

    Thornhill
    4 nights
    3.0 star property
    8.6/10 - Excellent (2,949 reviews)
    Return • Istanbul (IST) - Toronto (YYZ)
    IST - YYZ • Direct YYZ - IST • 1 stop
    AU$1,854
    AU$1,664
    per traveller
    found 19 hours ago
    Liberty Suites Hotel

Discover the most popular places to visit in Southwestern Ontario

Southwestern Ontario Hotel Deals

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.

Frequently Asked Questions

How much does a Southwestern Ontario holiday package cost?

Perhaps less than you might think — from a tempting AU$1,588, actually! By bundling flights, hotels and car rentals into a tailor-made travel package, your Southwestern Ontario escape is just clicks away.

How do I get a cheap travel package to Southwestern Ontario?

Bundling your flight and hotel with Expedia won't just save you time — it'll save you a pretty penny too. A Southwestern Ontario holiday package makes it a breeze to put together your perfect trip. With more than 550 airlines worldwide to pick from, finding flights that suit your schedule won't be a challenge. In addition to that, we have over 1 000 000 hotels globally to select from. Now that's choice! Whatever your budget, Expedia puts the world within your reach.

What are the top hotels in Southwestern Ontario?

For properties in Muskoka District with friendly service and comfy beds, check out Embassy Suites by Hilton Niagara Falls Fallsview and Sheraton Fallsview Hotel. If you're visiting Hamilton as well, you can look forward to a solid night's sleep at Hilton Niagara Falls/Fallsview Hotel & Suites or Oakes Hotel Overlooking the Falls.

How far in advance should I book my Southwestern Ontario holiday?

To score discount prices, book as early as you can. Air carriers usually release flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway to Southwestern Ontario, there are always plenty of great deals to be had on Expedia. Check them out now!

What does an Expedia Southwestern Ontario travel package include?

That depends entirely on you. You can select from a range of Southwestern Ontario bundles, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your ideal Southwestern Ontario getaway looks like, get set to save!

What should I know before booking a Southwestern Ontario travel package?

Our prices are always low. However, you'll grab even more savings if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and a huge range of choice.

Can I choose my airline with a Southwestern Ontario Expedia holiday package?

You certainly can. We offer more than 550 airline partners all over the world, so pick the carrier that's a good fit for your budget and travel needs.

If I'm not able to travel, can I cancel my Southwestern Ontario holiday package?

It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Southwestern Ontario holiday package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.