Southwestern Ontario Vacation Packages 2026 from $769

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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.

Town Inn Suites Hotel

Downtown Toronto

$769

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.6/10 Excellent! (3,870 reviews)

Staff was very accommodating about early check in, as our plane landed before noon on the day of check in.

Reviewed on Aug 12, 2026

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! (4,297 reviews)

New hotel in Toronto entertainment district. Conveniently located to lots of restaurants, entertainment venues and subway. Good breakfast buffet at the property. Room was comfortable and kept clean and staff friendly. There were a few issues (that might be associated with a new property). We had to mightily yank the room door shut to get the door to lock, for example (which was surprising for a brand new hotel). Also, the elevators didn’t seem to have sufficient capacity for their busiest time of day (9 am). The TV remote was difficult to use. It was little details like these that caused me to rate it as good rather than excellent.

Reviewed on Aug 13, 2026

1 Hotel Toronto

Downtown Toronto

$1,411

per person

Sep 25 - Sep 29

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (780 reviews)

Everything was amazing

Reviewed on Aug 10, 2026

Shangri-La Toronto

Downtown Toronto

$2,331

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)

Great location, excellent restaurant and helpful staff

Reviewed on Aug 12, 2026

Revery Toronto Downtown, Curio Collection by Hilton

Downtown Toronto

$928

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (1,316 reviews)

I would not recommend this hotel, especially if you are booking through Expedia. We booked through Expedia, and it felt like we were not given the same attention as other guests. We had to wait until 4:00 PM just to receive our room keys, while Holiday Inn members appeared to be given rooms first. There were several other disappointing issues: * The Wi-Fi was very poor and unreliable. * There was an unpleasant smell in the hotel/room. * The room had no proper view, and the windows offered almost no visibility. * There was no swimming pool. * The breakfast was very expensive. * Overall, the hotel felt overpriced for the facilities and service provided. * Most surprisingly, the bathroom door did not even have a lock, which is a basic privacy requirement. Considering the price, I expected much better service, facilities, cleanliness, and attention to guests. Unfortunately, the overall experience was disappointing and not worth the money.

Reviewed on Aug 12, 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

$62 nightly

$75 total

Aug 17 - Aug 18

Total with taxes and fees

8.6/10 Excellent! (3,347 reviews)

"More bar service and more tables open."

Reviewed on Aug 13, 2026

Hard Rock Hotel London Ontario

100 Kellogg Lane London ON

Fully refundableReserve now, pay when you stay

$193 nightly

$229 total

Aug 17 - Aug 18

Total with taxes and fees

9.4/10 Exceptional! (1,016 reviews)

"Great hotel and location for a family getaway. Clean and spacious rooms. Pool is"

Reviewed on Aug 12, 2026

See all 5,173 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.