Here are some useful questions for small talk on holidays. For the audio of these sentences and some language tips on one of the uses of "will" and comparatives; the use of the present perfect + "ever" in the UK and of the past simple + "ever" in the USA; and finally, the difference between "how…" and "what … like" questions, check out this TP Podcast episode.
Listen to these sentences at the Talking People Podcast
Tell me/us about your holiday
How was your holiday?
How were your holidays?
(for more detail in description)
What was it (your holiday) like?
What were they (your holidays) like?
What did you do?
Where did you go?
What presents did you get?
What presents did you give?
Did you get any money?
What did you buy with it?
What did you enjoy most?
What was the best/worst about your holiday?
What did you enjoy the least?
Did you go away? (leave the place where you live, on a trip)
(Why) Did you stay here?
Did you go away or did you stay here?
Did you do anything special?
What did you eat?
What else did you do?
What did you do on New Year’s Eve – that’s the 31st of December?
What did you do on New Year’s Day – that’s the first of January!?
Did you make any New Year’s Resolutions? Which?
(I’ll save more money, I’ll eat healthier, I’ll take some time off for myself…)
What did you do on Christmas Day -- on the 25th of December, I mean?
Did you have dinner with your family on Christmas Eve?
Do you open your presents then, or do you do that on the seventh of January?
Did you spend much, or were you able to stick to your budget?!
Did you buy many presents?
Did you buy your presents or did you make them?
What presents did you buy and who for?!
How many presents did each child get?
Did you make your own gift wrap?
Did you make any gifts?
Do you ever make your gifts?
Do you celebrate Christmas?
What holiday do you celebrate in the winter?
Which dates do you celebrate?
How do you celebrate the winter holidays?
Do you get together with your family or friends?
What are some of your family holiday traditions?
Tell us about your typical holiday festivities
What is your favorite (US) / favourite (UK) holiday?
Tell us about your favorite (US) / favourite (UK) holiday traditions
Do you know about any other traditions?
Do you get your gifts from Santa Claus or from the Three Wise Men?
What was the best gift you’ve ever got/received (UK)? Why?
What was the best gift you ever got/received (US)? Why?
Do you ever give away presents you got from somebody else?
Language Tip on the "How …? / What … like?" affair!
How…? Is used in health questions
How are you?
How’s your mum?
How’s your friend? (she was not feeling well the other day, for instance)
What … like? Is used to find out about somebody’s character (and looks, though for looks there’s the more straightforward "What … look like?")
What is your friend like? (her/his character – and looks) (I’d like to meet your friend but first I would like to know if we would get on, or if I would like her/his character /+ looks)
How…? / What…like? - for experiences
Sometimes there is not very much difference
How was your holiday?
Fine. I managed to survive!
What was your holiday like?
It was great!
Sometimes with the "how" phrase we just want to get a general comment -- it’s like an ice breaker, really! And then if we want to know more we turn to the "what was it like, then?" sentence, because it seems to imply we are expecting a longer description. But of course, this is no rule.
How…? / What…like? - for appearance
"How do I look?" is about checking if the outfit or make up you’re wearing is OK.
Fantastic! That outfit really suits you / You look great!
"What does he look like?" is about finding out what the body of that person looks like!
But the BBC offers a different explanation here, so check this out, please.