Users of cloud computing are increasingly overwhelmed with the wide range of providers and services offered by each provider. As such, many users select cloud services based on description alone. An emerging alternative is to use a decision support system (DSS), which typically relies on gaining insights from observational data in order to assist a customer in making decisions regarding optimal deployment or redeployment of cloud applications. The primary activity of such systems is the generation of a prediction model (e.g. using machine learning), which requires a significantly large amount of training data. However, considering the varying architectures of applications, cloud providers, and cloud offerings, this activity is not sustainable as it incurs additional time and cost to collect training data and subsequently train the models. We overcome this through developing a Transfer Learning (TL) approach where the knowledge (in the form of the prediction model and associated data set) gained from running an application on a particular cloud infrastructure is transferred in order to substantially reduce the overhead of building new models for the performance of new applications and/or cloud infrastructures. In this paper, we present our approach and evaluate it through extensive experimentation involving three real world applications over two major public cloud providers, namely Amazon and Google. Our evaluation shows that our novel two-mode TL scheme increases overall efficiency with a factor of 60\% reduction in the time and cost of generating a new prediction model. We test this under a number of cross-application and cross-cloud scenarios.