Southwestern Ontario Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 favourite with Southwestern Ontario travellers. 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.
Top Southwestern Ontario Vacation Deals
Price found within the past 48 hours. Click for updated prices.
StaysToronto
Downtown Toronto
CA $660
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Toronto (YYZ)
8/10 Very good! (33 reviews)
We had a wonderful stay with our two daughters! The apartment is in a great central location, making it easy to get around. We were also lucky enough to have a view of the CN Tower, which was a lovely bonus! The instructions for picking up and returning the keys were clear and easy to follow, so everything went smoothly. We had a great experience and would definitely stay here again on our next visit!
Reviewed on Oct 19, 2026
Hotel Riu Plaza Toronto
Downtown Toronto
CA $1,124
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Toronto (YYZ)
9.4/10 Exceptional! (4,956 reviews)
Excellent hotel. Parking was a concern but it was easy. Parked in the lot across the street. Breakfast was really good with lots of variety. Would definitely recommend.
Reviewed on Oct 20, 2026
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
Downtown London
Downtown London is known for its ample dining options, and you can make a stop by Centennial Hall and Grand Theatre while in the area.
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.
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 Waterloo Central Railway.
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.
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.
Ready to book your vacation to Southwestern Ontario?
Southwestern Ontario Hotel Deals
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
CA $71
CA $110 total
Oct 26 - Oct 27
includes taxes & fees
8.8/10 Excellent! (3,591 reviews)
"Everything was great, but because of the size and having two separate towers, there is a lot of moving around from checkin to parking to actually getting into your room."
Reviewed on Oct 21, 2026
Quality Inn
2899 King St E Kitchener ON
Fully refundableReserve now, pay when you stay
CA $105
CA $124 total
Oct 28 - Oct 29
includes taxes & fees
Waterfront Hotel Downtown Burlington
2020 Lakeshore Road Burlington ON
Fully refundableReserve now, pay when you stay
CA $161
CA $189 total
Nov 9 - Nov 10
includes taxes & fees
8.6/10 Excellent! (2,738 reviews)
"checked into our room and it immediately hit with a foul odour. lid to the toilet was broken and hanging on by one screw, bathroom sink did not drain at all. Advertised as having a pool and hottub but they don't. Hot tub sign was crossed out in sharpie and no longer there, the pool was closed. We ..."
Reviewed on Oct 20, 2026
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.
Stay near popular Southwestern Ontario attractions
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.
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.
Festival Theatre
9.6/10 (893 reviews)
You can get tickets for a performance at Festival Theatre on your trip to Stratford. Experience the acclaimed theater scene and lively festivals in this walkable area.
St Jacobs Farmers Market
9.2/10 (772 reviews)
During your visit to Township of Woolwich, you can do some window-shopping at St Jacobs Farmers Market. Experience the area's live music and festivals.
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.
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.
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.
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 great live music in this vibrant area.
Frequently asked questions
How much does a Southwestern Ontario vacation package cost?
Perhaps less than you might think — from a tempting CA $660, actually! By bundling flights, hotels and car rentals into a tailor-made travel package, your Southwestern Ontario escape is just clicks away.
How do I get a cheap travel package to Southwestern Ontario?
Bundling your flight and hotel with Expedia won't just save you time — it'll save you a pretty penny too. A Southwestern Ontario vacation package makes it a breeze to put together your perfect trip. With more than 550 airlines worldwide to pick from, finding flights that suit your schedule won't be a challenge. In addition to that, we have over 1,000,000 hotels globally to select from. Now that's choice! Whatever your budget, Expedia puts the world within your reach.
What are the top hotels in Southwestern Ontario?
For properties in Muskoka District with friendly service and comfy beds, check out Embassy Suites by Hilton Niagara Falls Fallsview and Sheraton Fallsview Hotel. If you're visiting Hamilton as well, you can look forward to a solid night's sleep at Hilton Niagara Falls/Fallsview Hotel & Suites or Oakes Hotel Overlooking the Falls.
How far in advance should I book my Southwestern Ontario vacation?
To score discount prices, book as early as you can. Air carriers usually release flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway to Southwestern Ontario, there are always plenty of great deals to be had on Expedia. Check them out now!
What does an Expedia Southwestern Ontario travel package include?
That depends entirely on you. You can select from a range of Southwestern Ontario bundles, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your ideal Southwestern Ontario getaway looks like, get set to save!
What should I know before booking a Southwestern Ontario travel package?
Our prices are always low. However, you'll grab even more savings if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and a huge range of choice.
Can I choose my airline with a Southwestern Ontario Expedia vacation package?
You certainly can. We offer more than 550 airline partners all over the world, so pick the carrier that's a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Southwestern Ontario vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Southwestern Ontario vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
Explore a world of travel with Expedia
- Tom Patterson Theatre
- Bronte Creek Provincial Park
- Watertown Vacations
- Theatre Aquarius
- Grand Bend Beach
- Queens Park
- Stratford City Hall
- Caledon Vacations
- Art Gallery of Hamilton
- Listowel Vacations
- Stratford Country Club
- Georgetown Vacations
- Waterloo Vacations
- Sleeman Centre
- African Lion Safari
- Caledon Ski Club
- St Jacobs Farmers Market
- Stratford Vacations
- Paris Vacations
- Waldie Blacksmith Shop
- Village Theatre Waterdown
- Halton Hills Vacations
- Rattlesnake Point
- The Egyptian Museum Mississauga
- Meadowvale Cemetery
- Legacy Pines Golf Club
- Brampton Memorial Arena
- Carisma Pentecostal Church
- Lionhead Golf & Country Club
- Milton Vacations
- Lake Aquitaine Park
- Dundas Valley Conservation Area
- Heartland Town Centre
- Mount Hope Vacations
- Mohawk College
- Oakville Vacations
- City View Park
- Lil' Monkeys
- Royal Botanical Gardens
- Mohawk Racetrack
- Brickman's Botanical Gardens
- Meadowvale Conservation Area
- Laurel Creek Conservation Area
- Sheridan College
- Ancaster Vacations
- Dundas Vacations
- Joshua Creek Heritage Art Centre
- Lester B. Pearson Memorial Theatre
- Fieldcote Memorial Park & Museum
- St. Jacobs Outlets
- Sheridan College Davis Campus
- Terra Cotta Conservation Area
- Kitchener Vacations
- New Hamburg Vacations
- Gage Park
- Glen Abbey Golf Course
- Festival Theatre
- Gage Park
- Td Coliseum
- St. Jacobs Market District Visitor Information Centre
- W. J. McCallion Planetarium
- Acton Vacations
- St. Jacobs Country Playhouse
- Saint Jacobs Vacations
- Conestoga Mall
- Christie Lake Conservation Area
- Erin Mills Vacations
- Caledon Country Club
- Avon Theatre
- Century Gardens Arena
- University of Guelph Arboretum
- Victoria Park
- Elora Vacations
- Lasalle Park
- Bronte Heritage Park
- Cathedral Basilica of Christ the King
- Stratford Municipal Golf Course
- Iskcon Brampton
- Flamborough Vacations
- Erin Vacations
- Flamboro Downs
- Elora Gorge Conservation Area
- Heart Lake Conservation Area
- Conestogo River Horseback Adventures
- Lazermania
- Hermitage Cascade
- Woodhurst Heights Park
- Steve Kerr Memorial Complex
- Riverdale Mennonite Church
- Tim Hortons Field
- Victoria Park Arena
- Burlington City Hall
- Downey's Farm Market
- Mcmaster University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
