Southwestern Ontario Vacations from $693

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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.
Upgraded Ensuite Rooms 7-min to Subway Near Downsview Rogers Stadium

Upgraded Ensuite Rooms 7-min to Subway Near Downsview Rogers Stadium

North York
$693
per person
Oct 1 - Oct 4
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Toronto (YYZ)
8.6/10 Excellent! (39 reviews)
Clean room, comfy bed. The SHOWER was AMAZING! I was able to wash some clothing quickly before a show. It's located in a perfect place close to food places, and a short walk to bus stops that can take you to the subway lines. The restaurants by the place are also really nice. It was perfect stay and comfortable.

Reviewed on Apr 9, 2026

1 Hotel Toronto

1 Hotel Toronto

Downtown Toronto
$1,847
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (789 reviews)
I brought my son to Toronto to watch the Yankees beat the Jays as a middle school graduation present. Unfortunately for us we did not see the Yankees win but the hotel was a huge win for us! Upon entering you are greeted by friendly staff and a relaxing aroma that really set the tone for our entire stay. Our room was wonderful. The older I get the less I handle traveling well because I find rooms to be dirty & very uncomfortable, I am the person who will typically clean the room myself upon arrival and I always stay at 4+ star hotels. As soon as I entered the room, everything just felt, looked & smelled clean. I had zero urge to clean (except the remote, which is a habit I will keep). The bed and pillows not only looked inviting, they were! Not too hard, not too soft for my aging body! There were eco-friendly elements everywhere, different woods sourced locally and the water on the entire property was filtered! Room service was very accommodating, one night we did not realize the time and ordered 3 minutes before closing. The gentleman was so kind, got our order to us and even remembered us the next time we ordered! Amazing! So many little things made this property worth every penny but I think what made it even more special was the little note and special treat they left for my son, congratulating him on his graduation! In this world today who does that?! They do! Highly recommend

Reviewed on Aug 30, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

Downtown Toronto
$1,039
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)
Great breakfast

Reviewed on Aug 30, 2026

Town Inn Suites Hotel

Town Inn Suites Hotel

Downtown Toronto
$933
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (3,961 reviews)
Holiday Inn Toronto - Int'l Airport by IHG

Holiday Inn Toronto - Int'l Airport by IHG

Etobicoke
$813
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.4/10 Very Good! (2,408 reviews)
Don’t book this property as they do not let you cancel a reservation and get refunded.

Reviewed on Aug 29, 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.

A red covered bridge over a river.

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.
Photo by Blue Mountain Resort

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.
Photo by Deanna Rodrigues

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

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 7 - Sep 8
Total with taxes and fees
Best Western Plus Lamplighter Inn & Conference Centre
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON
$60 nightly
$72 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (3,400 reviews)
"The mattress was kind of uncomfortable!"

Reviewed on Aug 29, 2026

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Sandman Hotel Hamilton

Sandman Hotel Hamilton

560 Centennial Parkway North Hamilton ON
Fully refundableReserve now, pay when you stay
$109 nightly
$128 total
Sep 3 - Sep 4
Total with taxes and fees
8.8/10 Excellent! (1,911 reviews)
"It will be nice if breakfast will be included."

Reviewed on Aug 30, 2026

Sandman Hotel Hamilton
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.

Find the Best Southwestern Ontario Vacation Packages

Southwestern Ontario Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Pearson Intl. Airport (YYZ)

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