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No, we don't usually have a problem to greet with every individual holiday. Why would we want to compact Hanukkah, Christmas and New Year into one "seasonal greeting"?
I thought that all those "happy holidays" and "seasonal greetings" is a product of "political correctness". If that is really so, then we most probably don't have something similar in our language (and I hope, we never will). We don't do much political correctness here, thank God.
Happy Holidays is a greeting said in some English-speaking regions, mostly in December. During this time it essentially means Happy New Year, and happy whatever of the 40 other December holidays you may or may not celebrate, because I don't necessarily want to assume it's Christmas, and/or because I don't celebrate Christmas but I wanted to say something nice. There are lots of assorted Christian holidays around this time, so even some conservative anglophones might say this. I also heard someone say Happy Holidays at the end of March when there were about to be several Christian and mostly-Catholic holidays ending with Easter Monday. On the exact day in question, people will often say a specific holiday greeting as a general, if sometimes-problematic, politeness.
I am curious how common kosmozhuk's sentiment is with younger and metropolitan Russian people who have more cultural awareness and exposure, plus general life opportunities. Considering females were forbidden from hundreds of professions in the modern world until 2019, and the cruel and dangerous claim that there are no gay people in the country, it seems kind of spot-on for the general populace. It also would be for half of the USA where the phrase "war on Christmas" was coined and still used by stubborn people who don't like change.
Every place has uplifting and distressing truths. Learning about them is a definite advantage and it helps with culturo-linguistic understanding of any language.
Well, I gave it a thought. And asked my colleagues.
С наступающим is usually used with New Year. That is grammatically correct phrase: С наступающим Новым Годом. Sometimes one can be greeted with "с наступающим праздником".
The only case of multiple holidays that I can think of is "майские праздники" - 1st of May and the Victory Day (9th of May). They are close together and there is a string or two of several non-working days. But we don't usually greet with "с майскими праздниками", V-Day is very special. We just use the term to designate some time period:
На майские праздники я поеду на дачу.
Встретимся после майских праздников.
Also we can use the word праздники to refer to several non-working days connected to one proper holiday. But not in a greeting manner.
No, it will be strange to use it for a few days off or a vacation. Праздник is something that people celebrate. A public or religious holiday, a local holiday or celebration, even your family celebration. Christmas, New Year, St. Valentine's day, Victory day, Teachers' Day (if you are a teacher), Mother's Day (if you are a mother), your wedding anniversary, etc. Saying "с праздником" is like saying "Happy New Year", only it works for any celebration.