Southwestern Ontario Vacation Packages 2026 from $603

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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.

The Waterside Inn

Port Credit

$603

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

New York (NYC) to Toronto (YYZ)

8.6/10 Excellent! (1,040 reviews)

I have nothing but amazing things to say about this property. The location is great, the staff are super helpful and the room was exactly what I needed. The combo washer/dryer was the cherry on top to my stay as I was stranded, thanks to westjet. Would definitely stay again.

Reviewed on Aug 14, 2026

1 Hotel Toronto

Downtown Toronto

$1,404

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (780 reviews)

Everything was absolutely PERFECT! The clean environment, the well kept rooms, the friendly staff and amazing food. Zero complaints and we can’t wait to return to Canada!

Reviewed on Aug 13, 2026

Shangri-La Toronto

Downtown Toronto

$2,326

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (1,324 reviews)

Cambridge Suites Toronto

Downtown Toronto

$1,426

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.2/10 Wonderful! (8,435 reviews)

Finlay House Bed and Breakfast Niagara - on - the - Lake

Old Town Historic District

$967

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (246 reviews)

Our stay was wonderful! The room was lovely and extremely comfortable. Yvonne was a perfect hostess, very friendly and welcoming. She answered all our questions and gave us great information on what to see and do. The breakfasts were delicious too, served promptly, and with great attention to detail. Overall, we couldn’t be more pleased with our stay and look forward to visiting again in the future!

Reviewed on Aug 1, 2026

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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)

Nothing says vacation like spending a lazy day at Grand Bend Beach, a popular beach 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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Scandinave Spa Blue Mountain

8.8/10 (775 reviews)

Scandinave Spa Blue Mountain is one of the more well-known attractions to visit during your trip 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

$116 nightly

$137 total

Aug 23 - Aug 24

Total with taxes and fees

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON

$68 nightly

$81 total

Aug 17 - Aug 18

Total with taxes and fees

8.6/10 Excellent! (3,355 reviews)

"Nice big room, very clean, great meal at Neros,"

Reviewed on Aug 14, 2026

Hard Rock Hotel London Ontario

100 Kellogg Lane London ON

Fully refundableReserve now, pay when you stay

$193 nightly

$229 total

Aug 16 - Aug 17

Total with taxes and fees

See all 5,190 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.