Southwestern Ontario Vacation Packages 2026 from $509

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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.

Living Water Resort and Spa

$509

per person

Nov 5 - Nov 8

found 6 hours ago

Roundtrip flight included

New York (NYC) to Toronto (YYZ)

8.4/10 Very Good! (1,594 reviews)

Spectacular Views Apartments

Downtown Toronto

Save 100% on your flight

$1,064

per person

Nov 7 - Nov 14

found 2 hours ago

Roundtrip flight included

Miami (MIA) to Toronto (YYZ)

8.8/10 Excellent! (52 reviews)

1 Hotel Toronto

Downtown Toronto

Save 100% on your flight

$1,371

per person

Dec 18 - Dec 23

found 9 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Toronto (YYZ)

9.4/10 Exceptional! (816 reviews)

Old Mill Toronto

Etobicoke

$679

per person

Nov 21 - Nov 25

found 8 hours ago

Roundtrip flight included

New York (NYC) to Toronto (YYZ)

9.4/10 Exceptional! (1,174 reviews)

Beautiful place to stay in Toronto.

Reviewed on Sep 27, 2026

Hotel Riu Plaza Toronto

Downtown Toronto

$638

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)

9.4/10 Exceptional! (4,688 reviews)

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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

A park with green grass, trees, benches, and a tall building in the background.

Downtown London

The urban hub of Ontario’s Western University features a variety of British-inspired attractions and the calm beauty of nature.

A river with buildings and a church tower in the background.

Paris

Explore Barker's Bush trails and admire rare Carolinian forests, then unwind at riverside restaurants while enjoying views of the illuminated Penman's Dam at night. Don't miss the historic Arlington Hotel and the charming cobblestone architecture.

A red brick building with arched windows and a sign reading "POWERHOUSE".

Stoney Creek

Explore the Bruce Trail, visit Battlefield Park, Devil's Punch Bowl, and Erland Lee Museum, or unwind at Fifty Point Conservation Area. Shop at Fiesta Mall and Eastgate Square Mall, with convenient access via Hamilton Street Railway.

Saint Jacobs

You'll enjoy the museums and riverfront in Saint Jacobs. You might want to make time for a stop at St. Jacobs Scoolhouse Theatre or Waterloo Central Railway.

A multi-tiered waterfall cascading over rocky steps.

Ancaster

Historic town on the Niagara Escarpment, Ancaster offers recreational centers like Morgan Firestone Arena and Ancaster Aquatic Centre, as well as sights such as Fieldcote Memorial Park and Museum, and the scenic Bruce Trail.

Stay near popular Southwestern Ontario attractions

A snow-covered ski resort at night with illuminated buildings and ski slopes.

Blue Mountain Ski Resort

9.0/10 (1,956 reviews)

From skiing and snow sports to mountain biking and zip-line tours, there are exciting activities throughout the year at this Ontario mountain resort.

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Two giraffes walking on a paved path in a grassy area with trees in the background.

African Lion Safari

8.2/10 (243 reviews)

Visit the native and exotic animals who live at African Lion Safari during your trip to Hamilton. While in this family-friendly area, you can savor the top-notch restaurants.

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A large circular building with a flat roof surrounded by a cityscape at night.

TD Coliseum

8.6/10 (402 reviews)

Catch an event at TD Coliseum during your trip to Hamilton. Experience the area's great live music and acclaimed theater scene.

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A lighthouse on a snowy shore with the ocean in the background.

Grand Bend Beach

9.0/10 (487 reviews)

Why not spend a carefree afternoon at Grand Bend Beach during your travels in Grand Bend? You can enjoy the restaurants while in the area.

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A river running through a town with a bridge, surrounded by dense greenery.

St Jacobs Farmers Market

9.2/10 (772 reviews)

During your visit to Township of Woolwich, you can do some window-shopping at St Jacobs Farmers Market. Experience the area's live music and festivals.

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A rocky coastline with a cave entrance and clear blue sea.

Bruce Peninsula National Park

9.6/10 (276 reviews)

Explore the great outdoors at Bruce Peninsula National Park, a lovely green space in Northern Bruce Peninsula. While you're in the area, stroll along the waterfront.

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Scandinave Spa Blue Mountain

8.8/10 (775 reviews)

You can take time to visit Scandinave Spa Blue Mountain during your travels to The Blue Mountains. Discover the mountain views in this quaint area, or enjoy its ski slopes.

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Detroit Windsor Tunnel

8.0/10 (1,568 reviews)

Find out about the history of Windsor when you spend time at Detroit Windsor Tunnel. Stroll along the riverfront or experience the great live music in this vibrant area.

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Southwestern Ontario Hotel Deals

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON

$59 nightly

$71 total

Oct 27 - Oct 28

Total with taxes and fees

Best Western Plus Lamplighter Inn & Conference Centre

591 Wellington Rd S. London ON

Fully refundableReserve now, pay when you stay

$101 nightly

$120 total

Oct 12 - Oct 13

Total with taxes and fees

8.8/10 Excellent! (1,946 reviews)

"…"

Reviewed on Sep 27, 2026

Waterfront Hotel Downtown Burlington

2020 Lakeshore Road Burlington ON

Fully refundableReserve now, pay when you stay

$95 nightly

$112 total

Oct 27 - Oct 28

Total with taxes and fees

8.6/10 Excellent! (2,692 reviews)

"Really great value for price. Proximity to waterfront walking and restaurants second to none. Very comfortable stay."

Reviewed on Sep 27, 2026

See all 5,230 properties in Southwestern Ontario

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.