The oldest part of Oosterbeek is the Benedendorp, on the northern bank of the Lower Rhine. One landmark in the village is the Hervormde Kerk, which has certain architectural sections that date back to the second half of the 10th century.
Oosterbeek was a separate municipality until 1818, when the area was divided between Doorwerth and the village of Renkum. In the 19th century, several mansions were built on the higher ground to the north of the old village. One of these mansions, called De Hemelse Berg, was destroyed in 1944. Another, called Hartenstein, is now home to the Airborne Museum. The construction of smaller buildings in the same area led to the creation of the Bovendorp. To the north of the built-up area lies the Arnhem Oosterbeek War Cemetery.
Oosterbeek is also the location of the Hotel de Bilderberg, where the Bilderberg Group first met in 1954.
The village is known for its involvement in the September 1944 Battle of Arnhem, during which it was heavily damaged. General Roy Urquhart of Britain had his headquarters at Hartenstein.
The Oosterbeek School is known as the birthplace of Dutch Impressionism, along with the nearby village of Wolfheze. Art historians call this the Barbizon of the North. The school's most successful period was from 1841 until 1870, before the artists turned to Laren, Kortenhoef, Egmond aan Zee, Katwijk aan Zee, Scheveningen, and Noordwijk, where they founded new art colonies or painters' villages. During this time, they established the Pulchri Studio in The Hague and opened the second Golden Age of Dutch painting. Consequently, they became the forerunners of the Modern art movement in the Netherlands.
Artists who were part of the movement near Oosterbeek include Gerard Bilders, Paul Gabriël, Barend Cornelis Koekkoek, Jacob Maris, Matthijs Maris, Willem Maris, Anton Mauve, Hendrik Mesdag, Willem Roelofs, and Jan Hendrik Weissenbruch.
Oosterbeek has a railway station that opened on 16 May 1845. It is on the Amsterdam–Arnhem railway (Rhijnspoorweg). Outside the station is a bus stop on a route that also goes to Arnhem.
The commemorative Airborne March is held in Oosterbeek every year on the first Saturday of September. The event started in 1947 and involves thousands of people, who walk 10 kilometers, 15 kilometers, or 25 kilometers. A 40-kilometer distance was added in the early 21st century.