This study aimed to determine the effect of different wood flooring layer structures and surface features on water intake, shrinkage, and swelling rates under different relative humidity and water retention conditions. Nine wood flooring sample types were tested: solid wood beech (Fagus orientalis L.) flooring covered with polyurethane varnish, four engineered wood flooring types having different core-layers (solid-wood poplar (Populus nigra L.), 23 medium-density fiberboard, and plywood) covered with ultraviolet dried polyurethane varnish on beech veneer, and four laminated wood flooring types having different core layers (high-density fiberboard, medium-density fiberboard, particleboard, and plywood). The results showed the lowest water retention increase rates for 2 and 24 hours in the high-density fiberboard and medium-density fiberboard core-layered laminated wood floorings. The lowest thickness swelling rate occurred in the laminated wood flooring with a plywood core layer during exposure to high relative humidity, whereas the lowest swelling rate in the width dimension occurred for laminated wood flooring compared with other product types. The lowest thickness shrinkage rate was in the poplar core-layered engineered wood flooring, whereas the lowest shrinkage rate in the width direction was in the medium-density fiberboard core-layered engineered wood flooring and plywood core-layered laminated wood flooring at lower relative humidities. In conclusion, high-density fiberboard and medium-density fiberboard core-layered laminated wood floorings are advisable for flooring exposed to a humid environment. All laminated wood flooring types provided good resistance to swelling. The plywood core-layered laminated wood floorings, poplar, and medium-density fiberboard core-layered engineered wood flooring types performed the best for low-humidity environments.