Southwestern Ontario Vacations from $555
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The Latest Southwestern Ontario Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Sterling Inn & Spa - an Ontario's Finest Inn
Sep 5 - Sep 8Sterling Inn & Spa - an Ontario's Finest Inn + Flight
Clifton Hill3 nights4.0 star property9.6/10 - Exceptional (2,456 reviews)"Great staffs and clean room"Reviewed July 31, 2026Roundtrip • Boston (BOS) - Toronto (YYZ)BOS - YTZ • Nonstop YTZ - BOS • Nonstop$751$555found 1 day agoper traveler - 1 Hotel Toronto
Sep 25 - Sep 291 Hotel Toronto + Flight
Downtown Toronto4 nights5.0 star property9.6/10 - Exceptional (779 reviews)"Highly recommend"Reviewed August 1, 2026Roundtrip • Boston (BOS) - Toronto (YYZ)BOS - YYZ • Nonstop YYZ - BOS • Nonstop$2,213$1,379found 1 day agoper traveler - Four Seasons Hotel Toronto
Sep 10 - Sep 13Four Seasons Hotel Toronto + Flight
Old Toronto3 nights5.0 star property9.6/10 - Exceptional (993 reviews)Roundtrip • Boston (BOS) - Toronto (YYZ)BOS - YYZ • Nonstop YYZ - BOS • Nonstop$1,929$1,279found 1 day agoper traveler - Hotel Riu Plaza Toronto
Sep 3 - Sep 7Hotel Riu Plaza Toronto + Flight
Downtown Toronto4 nights4.0 star property9.4/10 - Exceptional (4,256 reviews)Roundtrip • Boston (BOS) - Toronto (YYZ)BOS - YTZ • Nonstop YTZ - BOS • Nonstop - Finlay House Bed and Breakfast Niagara - on - the - Lake
Sep 5 - Sep 8Finlay House Bed and Breakfast Niagara - on - the - Lake + Flight
Old Town Historic District3 nights3.5 star property9.4/10 - Exceptional (245 reviews)"My wife and I just returned home from a lovely 3-night stay at the Finlay House B & B. We stayed in the Bernard Shaw bedroom, which accurately matched the attractive on-line photos. The room was very clean and well maintained, with a very comfortable king-sized bed. Hot and tasty breakfasts were served promptly each morning at 9:00 a.m. Each meal was unique, well balanced, and prepared with a creative flare. Great location if you are attending the Shaw Festival or just want to shop on Queen..."Reviewed July 30, 2026Roundtrip • Boston (BOS) - Toronto (YYZ)BOS - YTZ • Nonstop YTZ - BOS • Nonstop$761$557found 1 day agoper traveler
Discover the most popular places to visit in Southwestern Ontario
Southwestern Ontario Hotel Deals
9.6 out of 10, Exceptional, (1,749 reviews)
9.6/10
Exceptional
(1,749 reviews)
$96 nightly
The price is $115
$115 total
Aug 2 - Aug 3
Total with taxes and fees
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination4.0 star property
129.2 mi from Southwestern Ontario
8.6 out of 10, Excellent, (3,333 reviews)
8.6/10
Excellent
(3,333 reviews)
$71 nightly
The price is $85
$85 total
Aug 3 - Aug 4
Total with taxes and fees
9.0 out of 10, Wonderful, (2 reviews)
9.0/10
Wonderful
(2 reviews)
"This hotel is in the final stages of renovation. There final small fixtures yet to be installed (eg: light fixture and charging outlets on night table) for convenience. There are few hotels in this area, this upgraded facility will be needed. Outdoor amenities are a work in progress."
$57 nightly
The price is $65
$65 total
Aug 25 - Aug 26
Total with taxes and fees
9.4 out of 10, Exceptional, (1,751 reviews)
9.4/10
Exceptional
(1,751 reviews)
$101 nightly
The price is $119
$119 total
Aug 3 - Aug 4
Total with taxes and fees
Days Inn by Wyndham Sarnia Harbourfront
Days Inn by Wyndham Sarnia Harbourfront3.5 star property
76.9 mi from Southwestern Ontario
8.6 out of 10, Excellent, (1,282 reviews)
8.6/10
Excellent
(1,282 reviews)
"Room was cheap and worth the price. They allowed us to park the camper we pulled with no issue. The breakfast was really limited and very hot in the room it was set up in, but for the price I think it was still worth staying here. The room was nice and cold, and the bed was comfortable. Staff are nice and helpful"
$65 nightly
The price is $77
$77 total
Aug 9 - Aug 10
Total with taxes and fees
9.0 out of 10, Wonderful, (1,115 reviews)
9.0/10
Wonderful
(1,115 reviews)
$90 nightly
The price is $107
$107 total
Aug 9 - Aug 10
Total with taxes and fees
8.8 out of 10, Excellent, (2,347 reviews)
8.8/10
Excellent
(2,347 reviews)
$97 nightly
The price is $113
$113 total
Aug 16 - Aug 17
Total with taxes and fees
Holiday Inn Express Strathroy by IHG
Holiday Inn Express Strathroy by IHG2.5 star property
46.1 mi from Southwestern Ontario
9.6 out of 10, Exceptional, (497 reviews)
9.6/10
Exceptional
(497 reviews)
"Very good option if you’re heading somewhere in that neck of the woods.
We went to grand bend beach and stayed here, only 35 minute drive and I’m sure the best hotel option close to grand bend. Best price around for quality."
$121 nightly
The price is $136
$136 total
Aug 9 - Aug 10
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.