Roland von Hößlin was born in Munich into an old family of cavalry officers. In 1933, aged 17, he joined the Reichswehr and became an ensign ("Fahnenjunker") in Mounted Regiment 17 in Bamberg. In 1936, he was promoted to lieutenant. In 1939, during the Second World War, he took part in the Invasion of Poland as a first lieutenant and adjutant in Reconnaissance Detachment 10. He later had tank training at the Panzertruppenschule in Krampnitz, now part of Potsdam, and from March to July 1941 was a staff officer with the Afrika Korps staff in Tripolitania under Field Marshal Erwin Rommel. In August 1941,
Hößlin was named chief of the 3rd Reconnaissance Detachment 33, and in February 1942 he was promoted to captain. On 12 July 1942, he was badly wounded while commanding Reconnaissance Detachment 33 in action and was awarded the Knight's Cross of the Iron Cross (Ritterkreuz). His brother Hartmut von Hößlin was also awarded the Knight's Cross on 17 April 1945 as commander of II Artillery Regiment 7. By February 1944, Hößlin was commander of Officer-Candidate Training Detachment 24 based at Insterburg, East Prussia (now Chernyakhovsk in Russia's Kaliningrad Oblast). In April 1944, through his earlier friendship with Stauffenberg, he was let in on the 20 July Plotters' plans to overthrow Adolf Hitler. In the event of a successful coup d'état, Hößlin was to have his unit in Wehrkreis I (i.e., East Prussia) occupy important buildings and take other measures against the Nazi régime.
On 1 August 1944, a week and a half after the failed plot at the Wolf's Lair, came a transfer to Meiningen in Thuringia and a promotion to major. On 23 August 1944, however, Hößlin was arrested by the Gestapo, and shortly thereafter was ejected from the Wehrmacht. On 13 October 1944 came the sentencing by Roland Freisler at Hößlin's trial at the Volksgerichtshof. Freisler sentenced him to death for his part in the plot to assassinate Hitler, and Roland von Hößlin was hanged that same afternoon at Plötzensee Prison in Berlin. At Bamberg Cathedral, a plaque commemorates the five "Bamberg Troopers" – among them Roland von Hößlin – who gave their lives in the struggle against the Nazi régime.
- Knight's Cross of the Iron Cross on 23 July 1942 as Hauptmann and leader of Panzer-Aufklärungs-Abteilung 33.