1

In the following sentence:

If I won a holiday anywhere in the world, I would go to Japan.

Does 'holiday' simply means 'holiday', or does it mean a 'trip' or 'journey' or something else?

Thanks in advance.

2

Yes it means a trip to a place where you can spend your free time (a holiday):

Here is a real example:

Win a holiday to New York City - Terms and Conditions

2

In American and British English, one meaning of 'holiday' is "a day of festivity or recreation when no work is done": Christmas is a public holiday in many countries, and in British English it can also be used (singular 'holiday' or plural 'holidays') to mean the same as the American "vacation" - "an extended period of leisure and recreation, especially one spent away from home or in travelling": I had a holiday in China last year.

Holiday (Oxford Dictionaries)

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