There is no one size fits all answer to this question. How to water your orchids depends on a number of factors. It depends on the species of your orchid, it depends on the size of the container your orchid is in, it depends on the medium you are using and it depends on the climate / environment that your orchids are in.
Most orchids in cultivation today originate in tropical climates. As a rule of thumb, we want to emulate the natural conditions when it comes to giving water to your orchid. Tropical climates vary depending on the time of year, but are primarily warm and humid with a distinct rainy season and dry season. During the rainy season, an orchid can absorb water from rainfall and humidity, during the dry season, they absorb moisture from the humidity in the air, and can survive for a few months of relatively dry periods with low humidity in some parts of the tropics. Remember that most orchids typically grow in the canopy of trees, so rainfall is absorbed in slow drips to the leaves and roots, and absorbing moisture from dew and humidity in the air. Another thing to remember is that orchids tend to grow sideways with their leaves pointing downwards, which prevents rain from accumulating in the crown area. We never want to allow water to accumulate in the crown area. It is a good idea to spot dry any pools of water in the crown area or where the leaf and stem meet, especially in cooler climates.
The amount of water that your orchid needs can vary by species. One of the most common species of orchids is Phalaenopsis also known as moth orchid, which we will cover first. We want to water our Phalaenopsis when the medium and roots are dry. One way to tell if the roots are dry is to examine them. If the roots are dry, they are generally a silvery grayish color, and when they are saturated with water, they are generally green. This is why it is recommended to grow orchids in clear pots, so the roots can be monitored. We can then place the plastic pot inside an ornamental pot for more aesthetic pleasure. Another thing to note is if there is any condensation inside the clear pot, if there is, your orchid does not need to be watered yet. Also, press your finger into the medium to guage for dryness. A very common mistake for beginners is to overwater their orchid, which can lead to disease and death.
Let's talk about grow mediums for a moment in relation to how to water orchids. The three main types of grow medium that we use are, wood bark, sphagnum moss, and leca (lightweight expanded clay aggregate). We can use either of these mediums on their own or in a combination such as wood bark and moss. Each has different water retention characteristics and growers tend to favor the method that works best for them depending on the size of the container, the growth stage, the orchid itself or the environment.
Wood bark on its own or in combination with some sphagnum moss is the most common grow medium for orchids. In my opinion, this is the best and most forgiving grow medium for beginners. As to how to water your orchids, you can simply run it under the sink or use the aid of a watering can for ten to 15 seconds, giving the bark and roots a good soaking. Another method growers like to use if you live in a very dry area or where your orchid seems to dry out quickly, is to simply soak the orchid in another container or sink for ten to fifteen minutes, allowing the water to come about three quarters of the way up the container it is housed in. This allows the bark to become completely saturated, providing moisture for a number of days. Let the medium completely dry out between watering's. This can vary due to the size of the plant, the container, or the environment/climate of your region. In time, you will find what works best for you. Just remember that it is better to slightly err on the side of under watering than over watering.
Some growers like to use spagnum moss as their grow medium. Spagnum moss is an excellent grow medium, and there are conditions where moss is the best medium to use, such as for plants in small containers and for young seedlings where the root system has not yet developed. If you are a beginner, I would recommend that you stick with wood bark at first and experiment with spagnum moss later. One of the great benefits of spagnum moss is that it wicks moisture and distributes it evenly throughout the growing area. This can be helpful if you are finding that your wood bark medium is drying out on top, but staying moist at the bottom. Spagnum moss more evenly distributes water for your orchid. So, as to how to water orchids in moss, we can use less water than we would use with any other method as the moss absorbs the water and then wicks it, distributing the water more evenly. Depending on the size of our pot, this could be as little as a few tablespoons of water to a half cup or more. We can also set the pot in water for a few seconds and the moss at the bottom of the pot will absorb the water and wick it up throughout the medium. Let the moss dry between watering's, when moss is dry it has a crunchy, crackly sound to it and use this as a guage as to when to water your orchid. One drawback to moss is that it decomposes quickly and repotting will be necessary from time to time.
Leca or lightweight expanded clay aggregate is used for self watering partially hydroponic orchid growing. This is a relatively new way of growing orchids and works well for many orchid types. There are now a number of self watering systems that are currently being used for LECA. One is the cone method, where the LECA is allowed to drop into cone shaped openings in special pots, that dip into a water reservoir in the ornamental pot. The water is wicked up into the medium and keeps the LECA constantly moist providing a source of water, yet the sphere shape of the LECA allows for lots of air pockets keeping the roots relatively dry. Another method is the wick method, where cloth wicks are placed into the clay pellets and then extend down into a reservoir in an ornamental pot. One particular species that does not do well with self watering systems is the Vanda species. For more information on self watering systems visit this page.