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A street with historic buildings, cars, and a cyclist.

Southwestern Ontario Vacations from $637

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Top destinations in Southwestern Ontario

A lighthouse on a rocky island surrounded by clear water and autumn-colored trees.
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Tobermory

Tobermory

The Latest Southwestern Ontario Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 4 - Oct 9

    The Waterside Inn + Flight

    Port Credit
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,046 reviews)
    "I am giving this hotel 3 stars because I was not informed that the hotel was undergoing renovations. The balcony window in my room was completely covered by a tarp blocking the view and making the room feel dark and closed in. Other than that the room was clean and comfortable. Better communication about the renovations would have made the experience much better."
    Reviewed July 29, 2026
    Roundtrip • New York (NYC) - Toronto (YYZ)
    LGA - YKF • 1 stop YTZ - EWR • Nonstop
    $885
    $637
    per traveler
    found 1 day ago
    The Waterside Inn
  • Front of property
    Aug 30 - Sep 3

    Hotel Riu Plaza Toronto + Flight

    Downtown Toronto
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,229 reviews)
    "I’ve stayed at a few hotels over the years, but this is by far the nicest one. I did not see a speck of dust anywhere. Each and everyone of the staff members were extremely friendly and helpful. Another thing that caught my attention is the craftsmanship that went into putting this place together, the tiles , the trim, the amenities, all top tier and great quality. Luxurious and comfortable. Keep up the great work."
    Reviewed July 29, 2026
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YYZ • Nonstop YYZ - BOS • Nonstop
    $1,164
    $733
    per traveler
    found 2 days ago
    Hotel Riu Plaza Toronto
  • Terrace/patio
    Oct 9 - Oct 12

    The Hazelton Hotel Toronto + Flight

    Old Toronto
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YTZ • Nonstop YYZ - BOS • 1 stop
    $2,153
    $1,489
    per traveler
    found 2 days ago
    The Hazelton Hotel Toronto
  • Bar (on property)
    Sep 4 - Sep 6

    1 Hotel Toronto + Flight

    Downtown Toronto
    2 nights
    5.0 star property
    9.6/10 - Exceptional (775 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YTZ • Nonstop YTZ - BOS • Nonstop
    Save 100% on your flight
    $1,287
    $908
    per traveler
    found 2 days ago
    1 Hotel Toronto
  • Premium 1 Queen Bed, Balcony, Fireplace | Egyptian cotton sheets, premium bedding, minibar, blackout drapes
    Sep 4 - Sep 8

    Kent Motel Niagara on the Lake + Flight

    Queenston
    4 nights
    2.5 star property
    9.6/10 - Exceptional (343 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YKF • 1 stop YTZ - BOS • Nonstop
    $1,165
    $835
    per traveler
    found 1 day ago
    Kent Motel Niagara on the Lake

Discover the most popular places to visit in Southwestern Ontario

A snow-covered ski resort at night with illuminated buildings and ski slopes.
Photo by Blue Mountain Resort
Open 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.

Southwestern Ontario Hotel Deals

Exterior

Holiday Inn Express Hotel & Suites Waterloo - St Jacobs by IHG

Holiday Inn Express Hotel & Suites Waterloo - St Jacobs by IHG
2.5 star property
25.1 mi from Southwestern Ontario
8.8 out of 10, Excellent, (1,336 reviews)
"Central location minutes walking distance to St. Jacobs Market. Everything about this hotel is thoughtful in its design and service. The splash pad for the littles, the hot breakfast spread with all the classics, the 24/7 coffee bar, the towel hooks the shoe shine wipes/stain remover wipes, the spaciousness of the rooms, the comfy beds, the staff checking in and being friendly. Overall fantastic stay and will come again!"
$89 nightly
The price is $105
Aug 9 - Aug 10
Total with taxes and fees
Holiday Inn Express Hotel & Suites Waterloo - St Jacobs by IHG
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.
See all properties in Southwestern Ontario
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.