More than 200 Wakatipu patrons heard the Bathe in the River star perform with guitarist Tyson Smith.
It was largest audience so far in the winery's inaugural Summer Playground Series.
The Winehouse restaurant manager Ben Owens said the gig was "a huge success", helped by the sunshine and Smith's popularity among residents.
Queenstown favourite Anika Moa is lined up to perform on March 18 and she will conclude the series, after the scheduled final act, Julia Deans and Seth Haapu, was cancelled.
Tickets for Anika Moa cost $45 from Quest in Queenstown and Wanaka, the Arrowtown Information Centre, Eventfinder online and the venue.
Doors open at 5pm, the support act (to be announced) begins at 5.30pm, and Moa starts at 6pm.
Mr Owens said the Summer Playground Series would "definitely" return next year, although fewer acts, spread out more over the season, were likely.
