diff --git a/pandas/core/window/rolling.py b/pandas/core/window/rolling.py
index becbba703f92c..2d5fe7b8112ea 100644
--- a/pandas/core/window/rolling.py
+++ b/pandas/core/window/rolling.py
@@ -1884,6 +1884,13 @@ def _validate(self):
             else:
                 self._win_freq_i8 = freq.nanos
 
+            if self._on.dtype == "M8[us]":
+                self._win_freq_i8 /= 1e3
+            elif self._on.dtype == "M8[ms]":
+                self._win_freq_i8 /= 1e6
+            elif self._on.dtype == "M8[s]":
+                self._win_freq_i8 /= 1e9
+
             # min_periods must be an integer
             if self.min_periods is None:
                 self.min_periods = 1
diff --git a/pandas/tests/window/test_rolling.py b/pandas/tests/window/test_rolling.py
index 3fe922539780d..9eb2d544392bb 100644
--- a/pandas/tests/window/test_rolling.py
+++ b/pandas/tests/window/test_rolling.py
@@ -1950,3 +1950,25 @@ def test_numeric_only_corr_cov_series(kernel, use_arg, numeric_only, dtype):
         op2 = getattr(rolling2, kernel)
         expected = op2(*arg2, numeric_only=numeric_only)
         tm.assert_series_equal(result, expected)
+
+
+@pytest.mark.parametrize("unit", ["s", "ms", "us", "ns"])
+def test_rolling_rolling_max_window_nanoseconds_confilict_timestamp(unit):
+    # GH#55026
+    window = Timedelta(days=4)
+
+    ref_dates = date_range("2023-01-01", "2023-01-10", unit="ns")
+    ref_series = Series(0, index=ref_dates)
+    ref_series.iloc[0] = 1
+    ref_max_series = ref_series.rolling(window).max()
+
+    dates = date_range("2023-01-01", "2023-01-10", unit=unit)
+    series = Series(0, index=dates)
+    series.iloc[0] = 1
+    max_series = series.rolling(window).max()
+
+    ref_df = DataFrame(ref_max_series)
+    df = DataFrame(max_series)
+    df.index = df.index.as_unit("ns")
+
+    tm.assert_frame_equal(ref_df, df)