A user-friendly and affordable broad-band digital Near Infrared (NIR) camera (Canon PowerShot S110 NIR) was compared with a narrow-band reflectance spectrometer (USB2000, Ocean Optics) at leaf scale for monitoring changes in response to drought of three ecologically contrasting Quercus species (Q. robur, Q. pubescens, and Q. ilex). We aimed to (a) compare vegetation indices (VIs; that is: NDVI, Normalized Difference Vegetation Index; GNDVI, Green NDVI and NIRv, near-infrared reflectance of vegetation) retrieved by NIR-camera and spectrometer in order to test the reliability of a simple, low-cost, and rapid setup for widespread field applications; (b) to assess if NIR-camera VIs might be used to quantify water stress in oak seedlings; and (c) to track changes in leaf chlorophyll content. The study was carried out during a water stress test on 1-year-old seedlings in a greenhouse. The camera detected plant status in response to drought with results highly comparable to the visible/NIR (VIS/NIR) spectrometer (by calibration and standard geometry). Consistency between VIs and morpho-physiological traits was higher in Q. robur, the most drought-sensitive among the three species. Chlorophyll content was estimated with a high goodness-of-fit by VIs or reflectance bands in the visible range. Overall, NDVI performed better than GNDVI and NIRv, and VIs performed better than single bands. Looking forward, NIR-camera VIs are adequate for the early monitoring of drought stress in oak seedlings (or small trees) in the post-planting phase or in nursery settings, thus offering a new, reliable alternative for when costs are crucial, such as in the context of restoration programs.