The most significant sight in Vimperk is the chateau, originally built as a castle on the top of a high hill in the mid-13th century. The original structure survives only in the Vlček tower - a square donjon, and in part of the fortifications. Between 1530 and 1560 the castle was rebuilt into a Renaissance-style chateau, and in 1622 – 1624 a new part was added to it, including a long arcade section and another tower. The present shape of the castle is the result of a Baroque reconstruction in 1728 – 1734, and a repair following a fire in 1857. The complex of the castle includes the Haselburg artillery bastion, built in 1479 as an outpost of the castle, a good example of the late-medieval fortification architecture.
The Church of Our Lady of the Visitation, the town’s principal church situated in the lower part of the square, was originally an early-Gothic structure, rebuilt in the Gothic style in the second half of the 14th century, and made into a late-Gothic double-nave church after 1500. Part of the precious interior dates back to the 15th century. Of particular interest is the St. Innocent reliquary, containing human remains dating probably from antiquity. Next to the church is a late-Gothic town belfry from around 1500, rebuilt in 1909.
St. Bartholomew’s church was founded in the late 13th century and later adapted in the pseudo-Gothic style. Its interior treasures precious late-medieval wall paintings and tombstones dating from the 15th to the 17th century. Next to the church is the Fourteen Holy Helpers chapel, founded in 1708 by glassworks manager Michael Müller. The slope under the old cemetery bears a stone column supporting a sight well-worth noting - a sculptural group of St. Anne from the mid-16th century.
A large part of the late-Gothic fortifications from around 1479 were preserved to this day, particularly the section containing bastions above the river Volyňka, and under the castle. The towerlike Black Gate under the castle used to connect the town walls with the fortifications of the castle.
Among the remaining original burgher houses, the 16th-century U jelena house (Stag House, No 61), bearing a sculpture of a stag’s head on it, is of particular interest. Its front reflects Classicism, with remains of Rococo wall paintings, and its picturesqueness is underlined by an oriel supported by corbels. A large part of the original houses, namely those in the square, were destroyed in a great fire in 1904, one of the worst disasters in the town’s history, which took a heavy toll of five lives and 48 houses burnt down.
Log houses No. 16 and 18 are typical examples of the vernacular architecture of the Šumava region. They were thoroughly restored in the 20th century.