Originally Posted by
muji
I hadn't realized that the value of a free trip won was subject to income taxes. So, does this apply to winning just about any typical prize (vacation, weekend hotel stay, gift card)?

There ain't no free lunch here, sweetheart
For US residents, any win, whether a $10,000 trip or a 50cent coupon is subject to US income tax and should be reported on your tax return. If the value of the win is $600 or higher, the sponsor will ask for your social security number and issue a 1099, so yes, the IRS will know about it.
What your tax liability for wins will be depends on your individual tax bracket.
(I don't know how it works in Canada, so won't even try.)