Southwestern Ontario Vacations from $542

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Your Southwestern Ontario Vacation

When wanderlust beckons, answer it with a vacation 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 favorite with Southwestern Ontario travelers. 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 vacation. From flights and accommodations, to rental cars and activities, we know how to curate a travel experience like no other.

The Latest Southwestern Ontario vacation packages

Price found within the past 48 hours. Click for updated prices.
Woodbourne Inn
Waterfront Majesty Enclaves
Fairmont Royal York
1 Hotel Toronto
GLOBALSTAY. Modern Downtown Apartments
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Where to stay in Southwestern Ontario

Find the best Southwestern Ontario areas and neighborhoods for the activities you enjoy most. Learn more about Southwestern Ontario

Discover the most popular places to visit in Southwestern Ontario

Southwestern Ontario Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
$125 nightly
The price is $150 total per night from Sep 1 to Sep 2
$150 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (3,042 reviews)
"Clean rooms, having a fridge in the room was very helpful. Can go anywhere with the bus terminal just blocks away."

Reviewed on Aug 23, 2025

Caesars Windsor
Waterfront Hotel Downtown Burlington

Waterfront Hotel Downtown Burlington

3 out of 5
2020 Lakeshore Road, Burlington, ON
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $144 total per night from Aug 26 to Aug 27
$144 total
Aug 26 - Aug 27
Total with taxes and fees
8.4/10 Very Good! (2,392 reviews)
"Excellent"

Reviewed on Aug 23, 2025

Waterfront Hotel Downtown Burlington
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
$104 nightly
The price is $125 total per night from Sep 7 to Sep 8
$125 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (1,302 reviews)
"We really like it"

Reviewed on Aug 22, 2025

Holiday Inn Express Windsor Waterfront 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.

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