After working with such artists as Patti Page, Walt Weiskopf, Brian Lynch, Laverne Butler, Eric Alexander, and Hendrik Meurkens in 1993-1994, Bernstein returned to his solo work with Signs of Life. Issued in May of 1995, the album once again found the guitarist backed by pianist Mehldau, along with bassist Christian McBride, and drummer Gregory Hutchinson. Further work as a sideman with Ghetto Philharmonic, Trudy Desmond, Teodross Avery, Joshua Redman, Kevin Mahogany, Grant Stewart, and Mike LeDonne preceded the release of his third album, Brain Dance, in June 1997. This time, he led a quintet also containing organist Goldings, tenor saxophonist Eric Alexander, trombonist Steve Davis, and drummer Billy Drummond. Prior to his fourth album, Earth Tones, Bernstein recorded with Ralph Lalama and Eric Comstock, among others. Earth Tones, issued in August, 1998, found him fronting a trio with Goldings and drummer Bill Stewart.
Five years elapsed before the release of Heart's Content, Bernstein's fifth album as a leader, and he occupied the time working with a wide variety of musicians including Tom Aalfs, Group 15, Jimmy Cobb's Mob, David Bubba Brooks, Doug Lawrence, Sam Yahel, David Morgan, Jon Gordon, Michael Karn, Spike Wilner, Anna Lauvergnac, Harry Allen, Paula West, Nicholas Payton, Etta Jones, Béla Szakcsi Lakatos, Lee Konitz, Klaus Doldinger, and Ralph Bowen. Heart's Content, which was released in May 2003, was credited to "Peter Bernstein + 3," and the three were Mehldau, Bill Stewart, and bassist Larry Grenadier. The same year the album appeared, Bernstein could be heard on albums by Ryan Kisor, Wycliffe Gordon, Janis Siegel, and Martin Sasse, among others.
Stranger in Paradise, Bernstein's sixth album, was released in June 2004 by the Japanese Tokuma label, and employed the same lineup as that on Heart's Content. In addition to musicians with whom he had recorded before, Bernstein appeared on albums by Jim Rotondi and Dr. Lonnie Smith in 2004 and Kathy Kosins in 2005. On August 23, 2005, Mel Bay released the DVD Peter Bernstein Trio Live at Smoke, taped at a jazz club on the Upper West Side of Manhattan.
Among his many sideman sessions in the mid-2000s, Bernstein added dates with Joe Magnarelli, Alvin Queen, Planet Jazz, Anton Schwartz, John Pisano, David Fathead Newman, Don Friedman, Cory Weeds, and Andrew Suvalsky to the list of his credits, along with repeat appearances with others. In January 2009, the newly reactivated Xanadu label released Bernstein's seventh album, Monk, a tribute to Thelonious Monk featuring bassist Doug Weiss and drummer Bill Stewart.
In 2013, he paired with guitarist Joachim Schoenecker for the duo album Dialogues. A year later, he joined longtime associates Larry Goldings and Bill Stewart on Ramshackle Serenade. He then made his Smoke Sessions debut with 2016's Let Loose, a lively quartet date featuring pianist Gerald Clayton. Also that year, he collaborated with fellow guitarists Rale Micic, John Abercrombie, and Lage Lund on Inspired. For the guitarist's second Smoke Sessions date, Signs Live!, he reunited the band that had recorded his 1995 album Signs of Life, including pianist Brad Mehldau, bassist Christian McBride, and drummer Gregory Hutchinson. Released in 2017, Signs Live! was the first time Bernstein and the members of the quartet had all played together in over 20 years. ~ William Ruhlmann, Rovi