To be sparing or stingy with something; to begrudge spending or giving (money, goods, etc.).
彼は出費を惜しむタイプで、高い外食はめったにしない。
He's the sort of person who begrudges spending money and rarely eats out at expensive places.
会社は無駄なコストを惜しんで投資を見送った。
The company, reluctant to incur unnecessary costs, postponed the investment.
彼女は贈り物にお金を惜しまない。
She doesn't begrudge spending money on gifts.
To regret or lament; to feel that something unfortunate or regrettable has occurred.
試合で逆転負けしたのを多くのファンが惜しんだ。
Many fans lamented the come-from-behind loss in the match.
合格できなかったことを今でも惜しんでいる。
I still regret not being able to pass.
彼の急逝は多くの人に惜しまれた。
His sudden death was mourned/regretted by many people.
To be reluctant or unwilling to do something; to hesitate to take some action.
彼は新しい職に移るのを惜しんで決断を先延ばしにした。
He hesitated to move to the new job and postponed his decision.
休日を潰してまで手伝うのを惜しんだ。
He was reluctant to help if it meant giving up his day off.
To value or prize something; to regard someone or something as precious.
故人を惜しんで、式場には多くの花が飾られていた。
In memory of the deceased, many flowers were displayed at the venue.
彼女は古い写真を惜しんで手放さなかった。
She treasured the old photos and wouldn't part with them.
Archaic/literary meaning: to love or cherish (used in classical/literary Japanese).
和歌などでは『惜しむ』が愛するの意味で用いられる例がある。
In waka and other classical poems, '惜しむ' is sometimes used to mean 'to love'.