Southwestern Ontario Vacation Packages 2026 from $939

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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.

One King West Hotel & Residence

Downtown Toronto

Save 100% on your flight

$939

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (8,386 reviews)

Hotel Riu Plaza Toronto

Downtown Toronto

$1,302

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (4,484 reviews)

Fabulous room on floor 21. Breakfast was amazing but go early. Amazing stay. One of the best hotels in Toronto I have stayed in.

Reviewed on Aug 27, 2026

Town Inn Suites Hotel

Downtown Toronto

$1,048

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.6/10 Excellent! (3,932 reviews)

Great location, suite had tonnes of space, felt modern and updated, but man the matresses were not great. Super friendly staff. Parking on site.

Reviewed on Aug 27, 2026

1 Hotel Toronto

Downtown Toronto

$1,440

per person

Nov 5 - Nov 9

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (786 reviews)

Park Hyatt Toronto

Old Toronto

$2,510

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.2/10 Wonderful! (1,009 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 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 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 narrow waterway with a wooden bridge, surrounded by lush green fields and a distant tree line.

Point Pelee National Park

9.6/10 (480 reviews)

Hike through marshes and jungle-like environs and visit mainland Canada’s southernmost point in this small but impressive national park.

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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

Best Western Plus Lamplighter Inn & Conference Centre

591 Wellington Rd S. London ON

Fully refundableReserve now, pay when you stay

$110 nightly

$130 total

Sep 7 - Sep 8

Total with taxes and fees

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON

$71 nightly

$85 total

Sep 2 - Sep 3

Total with taxes and fees

Hard Rock Hotel London Ontario

100 Kellogg Lane London ON

Fully refundableReserve now, pay when you stay

$206 nightly

$244 total

Sep 6 - Sep 7

Total with taxes and fees

9.4/10 Exceptional! (1,074 reviews)

"We like everything in the hotel, this is our second time here and we went back to 1913 restaurant but this time, please "BE AWARE", even it's a fancy restaurant, my son almost got choke from the milkshake, there's a sudden sharp tiny broken plastic went to his mouth, he kept chewing it and find out ..."

Reviewed on Aug 27, 2026

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.