Planning a holiday with three generations

The hardest holidays to plan are the ones with the widest age range. Someone needs a nap, someone needs a pool, someone needs a chair in the shade and a conversation. A resort makes you co-ordinate all of that across rooms and mealtimes. A house does not.

Stairs are the first question

Ask before you book, not after. Some houses are single-storey and some are built into a hillside on three levels. If a grandparent is coming, that one detail matters more than the view — and we will tell you straight which of ours works.

Let the day split

The point of a house is that it can hold several different afternoons at once. Children in the pool, one parent with them, somebody asleep upstairs, somebody else reading on a terrace. Nobody has to be entertained on the same schedule.

Food is the easy part

Tell the kitchen about the child who eats almost nothing and the grandparent who cannot manage chilli. It is a kitchen in a house — it cooks for your group, not for a dining room of strangers. Do it when you book rather than on arrival.

Build in a day with nothing in it

The most common mistake is one outing per day for the whole trip. With a wide age range, one thing every other day is plenty, and the empty days are usually the ones people remember.

Ask about the things nobody lists

Whether the pool has shade at midday. Whether the bedrooms are near each other or at opposite ends. Whether there is somewhere quiet to sit that is not a bedroom. Ask us — we have stayed in these houses.