In recent decades, Skylark (Alauda arvensis) populations in Europe have declined sharply due to agricultural intensification. Insufficient reproduction rates are one reason. Increased winter mortality may also be important, but studies outside the breeding season are scarce and mostly limited to the UK. We studied habitat selection of wintering Skylarks in an agricultural area in the Netherlands. We monitored Skylarks between November 2008 and March 2009 on 10 survey plots including 77 different arable fields and permanent grasslands and covering in total 480 ha. We simultaneously measured food availability, vegetation structure and field boundary characteristics. We also analysed 158 faecal pellets collected on potato and cereal stubble fields to relate Skylark diet to seasonal changes in food availability and foraging habitat. We show that cereal stubble fields larger than 4.3 ha, surrounded by no or low boundary vegetation and a density of dietary seeds of more than 860 seeds m(-2), were most suitable for wintering Skylarks. Skylark group densities were low on permanent grasslands and on maize stubble fields. Densities of dietary seeds were highest in soils of potato stubble fields followed by cereal stubble fields, grasslands and maize stubble fields. Skylarks showed a strong preference for cereal grains, but their proportion in the diet fell sharply at the end of November, indicating that cereal grains were depleted and birds had to switch to less profitable food sources, such as weed seeds and leaves. We conclude that Skylarks wintering in agricultural landscapes possibly suffer from a lack of energy-rich food sources and only a few fields provide sufficient food. Conservation measures should strive to improve the wintering situation by creating food-rich habitats such as over-winter stubble with a rich layer of weeds on large fields and localised in open areas.