diff --git a/doc/source/whatsnew/v2.2.0.rst b/doc/source/whatsnew/v2.2.0.rst
index f155fb27d0de5..7f81f040e92d4 100644
--- a/doc/source/whatsnew/v2.2.0.rst
+++ b/doc/source/whatsnew/v2.2.0.rst
@@ -395,6 +395,7 @@ Other Deprecations
 - Deprecated strings ``T``, ``S``, ``L``, ``U``, and ``N`` denoting frequencies in :class:`Minute`, :class:`Second`, :class:`Milli`, :class:`Micro`, :class:`Nano` (:issue:`52536`)
 - Deprecated the ``errors="ignore"`` option in :func:`to_datetime`, :func:`to_timedelta`, and :func:`to_numeric`; explicitly catch exceptions instead (:issue:`54467`)
 - Deprecated the ``fastpath`` keyword in the :class:`Series` constructor (:issue:`20110`)
+- Deprecated the ``kind`` keyword in :meth:`Series.resample` and :meth:`DataFrame.resample`, explicitly cast the object's ``index`` instead (:issue:`55895`)
 - Deprecated the ``ordinal`` keyword in :class:`PeriodIndex`, use :meth:`PeriodIndex.from_ordinals` instead (:issue:`55960`)
 - Deprecated the extension test classes ``BaseNoReduceTests``, ``BaseBooleanReduceTests``, and ``BaseNumericReduceTests``, use ``BaseReduceTests`` instead (:issue:`54663`)
 - Deprecated the option ``mode.data_manager`` and the ``ArrayManager``; only the ``BlockManager`` will be available in future versions (:issue:`55043`)
diff --git a/pandas/core/generic.py b/pandas/core/generic.py
index 0d95d197815d3..c4b333c8a22ca 100644
--- a/pandas/core/generic.py
+++ b/pandas/core/generic.py
@@ -9217,7 +9217,7 @@ def resample(
         closed: Literal["right", "left"] | None = None,
         label: Literal["right", "left"] | None = None,
         convention: Literal["start", "end", "s", "e"] = "start",
-        kind: Literal["timestamp", "period"] | None = None,
+        kind: Literal["timestamp", "period"] | None | lib.NoDefault = lib.no_default,
         on: Level | None = None,
         level: Level | None = None,
         origin: str | TimestampConvertibleTypes = "start_day",
@@ -9259,6 +9259,9 @@ def resample(
             `DateTimeIndex` or 'period' to convert it to a `PeriodIndex`.
             By default the input representation is retained.
 
+            .. deprecated:: 2.2.0
+                Convert index to desired type explicitly instead.
+
         on : str, optional
             For a DataFrame, column to use instead of index for resampling.
             Column must be datetime-like.
@@ -9616,6 +9619,18 @@ def resample(
         else:
             axis = 0
 
+        if kind is not lib.no_default:
+            # GH#55895
+            warnings.warn(
+                f"The 'kind' keyword in {type(self).__name__}.resample is "
+                "deprecated and will be removed in a future version. "
+                "Explicitly cast the index to the desired type instead",
+                FutureWarning,
+                stacklevel=find_stack_level(),
+            )
+        else:
+            kind = None
+
         return get_resampler(
             cast("Series | DataFrame", self),
             freq=rule,
diff --git a/pandas/tests/io/excel/test_writers.py b/pandas/tests/io/excel/test_writers.py
index 22cd0621fd4c4..bf56f054812e0 100644
--- a/pandas/tests/io/excel/test_writers.py
+++ b/pandas/tests/io/excel/test_writers.py
@@ -767,7 +767,9 @@ def test_to_excel_timedelta(self, path):
         tm.assert_frame_equal(expected, recons)
 
     def test_to_excel_periodindex(self, path):
-        xp = tm.makeTimeDataFrame()[:5].resample("ME", kind="period").mean()
+        # xp has a PeriodIndex
+        df = tm.makeTimeDataFrame()[:5]
+        xp = df.resample("ME").mean().to_period("M")
 
         xp.to_excel(path, sheet_name="sht1")
 
diff --git a/pandas/tests/resample/test_datetime_index.py b/pandas/tests/resample/test_datetime_index.py
index 98cd7d7ae22f6..865c02798c648 100644
--- a/pandas/tests/resample/test_datetime_index.py
+++ b/pandas/tests/resample/test_datetime_index.py
@@ -455,7 +455,9 @@ def test_resample_frame_basic_M_A(freq, unit):
 def test_resample_frame_basic_kind(freq, unit):
     df = tm.makeTimeDataFrame()
     df.index = df.index.as_unit(unit)
-    df.resample(freq, kind="period").mean()
+    msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        df.resample(freq, kind="period").mean()
 
 
 def test_resample_upsample(unit):
@@ -687,7 +689,9 @@ def test_resample_timestamp_to_period(
     ts = simple_date_range_series("1/1/1990", "1/1/2000")
     ts.index = ts.index.as_unit(unit)
 
-    result = ts.resample(freq, kind="period").mean()
+    msg = "The 'kind' keyword in Series.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        result = ts.resample(freq, kind="period").mean()
     expected = ts.resample(freq).mean()
     expected.index = period_range(**expected_kwargs)
     tm.assert_series_equal(result, expected)
@@ -1020,7 +1024,9 @@ def test_resample_to_period_monthly_buglet(unit):
     rng = date_range("1/1/2000", "12/31/2000").as_unit(unit)
     ts = Series(np.random.default_rng(2).standard_normal(len(rng)), index=rng)
 
-    result = ts.resample("ME", kind="period").mean()
+    msg = "The 'kind' keyword in Series.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        result = ts.resample("ME", kind="period").mean()
     exp_index = period_range("Jan-2000", "Dec-2000", freq="M")
     tm.assert_index_equal(result.index, exp_index)
 
@@ -1139,14 +1145,18 @@ def test_resample_anchored_intraday(unit):
     df = DataFrame(rng.month, index=rng)
 
     result = df.resample("ME").mean()
-    expected = df.resample("ME", kind="period").mean().to_timestamp(how="end")
+    msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        expected = df.resample("ME", kind="period").mean().to_timestamp(how="end")
     expected.index += Timedelta(1, "ns") - Timedelta(1, "D")
     expected.index = expected.index.as_unit(unit)._with_freq("infer")
     assert expected.index.freq == "ME"
     tm.assert_frame_equal(result, expected)
 
     result = df.resample("ME", closed="left").mean()
-    exp = df.shift(1, freq="D").resample("ME", kind="period").mean()
+    msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        exp = df.shift(1, freq="D").resample("ME", kind="period").mean()
     exp = exp.to_timestamp(how="end")
 
     exp.index = exp.index + Timedelta(1, "ns") - Timedelta(1, "D")
@@ -1160,7 +1170,9 @@ def test_resample_anchored_intraday2(unit):
     df = DataFrame(rng.month, index=rng)
 
     result = df.resample("QE").mean()
-    expected = df.resample("QE", kind="period").mean().to_timestamp(how="end")
+    msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        expected = df.resample("QE", kind="period").mean().to_timestamp(how="end")
     expected.index += Timedelta(1, "ns") - Timedelta(1, "D")
     expected.index._data.freq = "QE"
     expected.index._freq = lib.no_default
@@ -1168,7 +1180,11 @@ def test_resample_anchored_intraday2(unit):
     tm.assert_frame_equal(result, expected)
 
     result = df.resample("QE", closed="left").mean()
-    expected = df.shift(1, freq="D").resample("QE", kind="period", closed="left").mean()
+    msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        expected = (
+            df.shift(1, freq="D").resample("QE", kind="period", closed="left").mean()
+        )
     expected = expected.to_timestamp(how="end")
     expected.index += Timedelta(1, "ns") - Timedelta(1, "D")
     expected.index._data.freq = "QE"
@@ -1225,7 +1241,9 @@ def test_corner_cases_date(simple_date_range_series, unit):
     # resample to periods
     ts = simple_date_range_series("2000-04-28", "2000-04-30 11:00", freq="h")
     ts.index = ts.index.as_unit(unit)
-    result = ts.resample("ME", kind="period").mean()
+    msg = "The 'kind' keyword in Series.resample is deprecated"
+    with tm.assert_produces_warning(FutureWarning, match=msg):
+        result = ts.resample("ME", kind="period").mean()
     assert len(result) == 1
     assert result.index[0] == Period("2000-04", freq="M")
 
diff --git a/pandas/tests/resample/test_period_index.py b/pandas/tests/resample/test_period_index.py
index 5d233a940de2f..b66c2ff02a35d 100644
--- a/pandas/tests/resample/test_period_index.py
+++ b/pandas/tests/resample/test_period_index.py
@@ -77,7 +77,9 @@ def test_asfreq(self, series_and_frame, freq, kind):
             end = (obj.index[-1] + obj.index.freq).to_timestamp(how="start")
             new_index = date_range(start=start, end=end, freq=freq, inclusive="left")
             expected = obj.to_timestamp().reindex(new_index).to_period(freq)
-        result = obj.resample(freq, kind=kind).asfreq()
+        msg = "The 'kind' keyword in (Series|DataFrame).resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = obj.resample(freq, kind=kind).asfreq()
         tm.assert_almost_equal(result, expected)
 
     def test_asfreq_fill_value(self, series):
@@ -90,7 +92,9 @@ def test_asfreq_fill_value(self, series):
             freq="1h",
         )
         expected = s.to_timestamp().reindex(new_index, fill_value=4.0)
-        result = s.resample("1h", kind="timestamp").asfreq(fill_value=4.0)
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = s.resample("1h", kind="timestamp").asfreq(fill_value=4.0)
         tm.assert_series_equal(result, expected)
 
         frame = s.to_frame("value")
@@ -100,7 +104,9 @@ def test_asfreq_fill_value(self, series):
             freq="1h",
         )
         expected = frame.to_timestamp().reindex(new_index, fill_value=3.0)
-        result = frame.resample("1h", kind="timestamp").asfreq(fill_value=3.0)
+        msg = "The 'kind' keyword in DataFrame.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = frame.resample("1h", kind="timestamp").asfreq(fill_value=3.0)
         tm.assert_frame_equal(result, expected)
 
     @pytest.mark.parametrize("freq", ["h", "12h", "2D", "W"])
@@ -119,8 +125,10 @@ def test_selection(self, index, freq, kind, kwargs):
             r"not currently supported, use \.set_index\(\.\.\.\) to "
             "explicitly set index"
         )
+        depr_msg = "The 'kind' keyword in DataFrame.resample is deprecated"
         with pytest.raises(NotImplementedError, match=msg):
-            df.resample(freq, kind=kind, **kwargs)
+            with tm.assert_produces_warning(FutureWarning, match=depr_msg):
+                df.resample(freq, kind=kind, **kwargs)
 
     @pytest.mark.parametrize("month", MONTHS)
     @pytest.mark.parametrize("meth", ["ffill", "bfill"])
@@ -250,9 +258,12 @@ def test_resample_basic(self):
             name="idx",
         )
         expected = Series([34.5, 79.5], index=index)
-        result = s.to_period().resample("min", kind="period").mean()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = s.to_period().resample("min", kind="period").mean()
         tm.assert_series_equal(result, expected)
-        result2 = s.resample("min", kind="period").mean()
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result2 = s.resample("min", kind="period").mean()
         tm.assert_series_equal(result2, expected)
 
     @pytest.mark.parametrize(
@@ -307,7 +318,9 @@ def test_with_local_timezone(self, tz):
 
         series = Series(1, index=index)
         series = series.tz_convert(local_timezone)
-        result = series.resample("D", kind="period").mean()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = series.resample("D", kind="period").mean()
 
         # Create the expected series
         # Index is moved back a day with the timezone conversion from UTC to
@@ -406,7 +419,9 @@ def test_weekly_upsample(self, day, target, convention, simple_period_range_seri
     def test_resample_to_timestamps(self, simple_period_range_series):
         ts = simple_period_range_series("1/1/1990", "12/31/1995", freq="M")
 
-        result = ts.resample("Y-DEC", kind="timestamp").mean()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = ts.resample("Y-DEC", kind="timestamp").mean()
         expected = ts.to_timestamp(how="start").resample("YE-DEC").mean()
         tm.assert_series_equal(result, expected)
 
@@ -466,7 +481,9 @@ def test_resample_5minute(self, freq, kind):
         expected = ts.to_timestamp().resample(freq).mean()
         if kind != "timestamp":
             expected = expected.to_period(freq)
-        result = ts.resample(freq, kind=kind).mean()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = ts.resample(freq, kind=kind).mean()
         tm.assert_series_equal(result, expected)
 
     def test_upsample_daily_business_daily(self, simple_period_range_series):
@@ -540,7 +557,9 @@ def test_resample_tz_localized2(self):
         tm.assert_series_equal(result, expected)
 
         # for good measure
-        result = s.resample("D", kind="period").mean()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = s.resample("D", kind="period").mean()
         ex_index = period_range("2001-09-20", periods=1, freq="D")
         expected = Series([1.5], index=ex_index)
         tm.assert_series_equal(result, expected)
@@ -785,7 +804,9 @@ def test_upsampling_ohlc(self, freq, period_mult, kind):
         # of the last original period, so extend accordingly:
         new_index = period_range(start="2000", freq=freq, periods=period_mult * len(pi))
         expected = expected.reindex(new_index)
-        result = s.resample(freq, kind=kind).ohlc()
+        msg = "The 'kind' keyword in Series.resample is deprecated"
+        with tm.assert_produces_warning(FutureWarning, match=msg):
+            result = s.resample(freq, kind=kind).ohlc()
         tm.assert_frame_equal(result, expected)
 
     @pytest.mark.parametrize(