Southwestern Ontario Vacation Packages 2026 from $478

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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.

Sterling Inn & Spa - an Ontario's Finest Inn

Clifton Hill

$478

per person

Oct 9 - Oct 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (2,508 reviews)

Our stay at the Sterling was absolutely beautiful, breakfast in bed complementary every morning. Thank you so much for upgrading our room for my big 60th birthday party. What a special treat. It was so close to Niagara Falls. You could walk pretty much anywhere, but it was safe and secure. The staff at the front desk was always so welcoming and so friendly and offered to help us out anytime we needed some suggestions. The AG Inspired Cuisine downstairs was amazing. Farm to table and presentation was .

Reviewed on Sep 2, 2026

1 Hotel Toronto

Downtown Toronto

$2,101

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (789 reviews)

Beautiful place and the staff were very helpful

Reviewed on Sep 2, 2026

Hotel Riu Plaza Toronto

Downtown Toronto

$921

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (4,590 reviews)

One King West Hotel & Residence

Downtown Toronto

Save 100% on your flight

$966

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (8,419 reviews)

The Waterside Inn

Port Credit

$600

per person

Oct 12 - Oct 17

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.6/10 Excellent! (1,084 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 Maple Syrup Museum of Ontario.

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 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 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 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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A pianist performing on a grand piano in a dimly lit concert hall with an audience in the background.

Festival Theatre

9.6/10 (893 reviews)

You can get tickets for a performance at Festival Theatre on your trip to Stratford. Experience the lively festivals and entertainment choices in this walkable area.

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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 acclaimed art scene 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

$66 nightly

$79 total

Sep 7 - Sep 8

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

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

Sandman Hotel Hamilton

560 Centennial Parkway North Hamilton ON

Fully refundableReserve now, pay when you stay

$96 nightly

$113 total

Oct 4 - Oct 5

Total with taxes and fees

See all 5,228 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.