The aim of this work was to study the combined effect of ultra-high pressure homogenization (UHPH) and β-cyclodextrin (β-CD) on cholesterol removal from bovine raw milk. Whole raw milk (3.87% ± 0.49% fat) was submitted to UHPH (0, 100, 200,and 300 MPa) and the addition of β-CD (0%, 0.1%, 0.3%, and 0.6%). Cholesterol removal increased with β-CD concentration and pressure applied. For 0.6% β-CD and 100 MPa, cholesterol removal was 65%; the highest cholesterol removal was obtained for 0.6% β-CD and 200–300 MPa reaching 87%–89%. Aggregation phenomena caused y UHPH (300 MPa) did not affect complex formation, whereas β-CD binding increased above 0.3%. UHPH increased L* and reduced b* color parameters. UHPH reduced 3 log cfu/ml of total aerobic counts. Cholesterol reduced milk produced under selected conditions (200 MPa, 0.6% β-CD) was comparable in terms of consumer acceptance to commercial pasteurized or UHT milks.