Prince Obolensky may refer to:

• Prince Alexander Sergeevich Obolensky (1916–1940), son of Serge Obolensky and Princess Luba and England rugby union international
• Prince Dimitri Alexandrovich Obolensky (1882–1964), Russian landowner
• Prince Dimitri Obolensky (1918–2001), son of Prince Dimitri Alexandrovich Obolensky (1882–1964) and Countess Maria Shuvalov (1894–1973)
• Prince Ivan Mikhailovich Obolensky (1853–1910), Governor-General of Finland
• Prince Michael Alexander Obolensky, American pretender
• Prince Serge Obolensky (1890–1978), husband of Ava Alice Muriel Astor, and son of Platon Obolensky and Marie Narishkin