diff --git a/CHANGELOG.md b/CHANGELOG.md
index dbbcae7a..d593c788 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@ and this project adheres to [Semantic Versioning](http://semver.org/spec/v2.0.0.
 
 ## [Unreleased]
 ### Added
+- Add conversions between `OsStr`/`OsString`/`Path`/`PathBuf` and Python strings. [#1379](https://github.com/PyO3/pyo3/pull/1379)
 - Add FFI definition `PyCFunction_CheckExact` for Python 3.9 and later. [#1425](https://github.com/PyO3/pyo3/pull/1425)
 
 ### Changed
diff --git a/guide/src/conversions/tables.md b/guide/src/conversions/tables.md
index 72768a6f..a7fada47 100644
--- a/guide/src/conversions/tables.md
+++ b/guide/src/conversions/tables.md
@@ -13,7 +13,7 @@ The table below contains the Python type and the corresponding function argument
 | Python        | Rust                            | Rust (Python-native) |
 | ------------- |:-------------------------------:|:--------------------:|
 | `object`      | -                               | `&PyAny`             |
-| `str`         | `String`, `Cow<str>`, `&str`    | `&PyUnicode`         |
+| `str`         | `String`, `Cow<str>`, `&str`, `OsString`, `PathBuf` | `&PyUnicode` |
 | `bytes`       | `Vec<u8>`, `&[u8]`              | `&PyBytes`           |
 | `bool`        | `bool`                          | `&PyBool`            |
 | `int`         | Any integer type (`i32`, `u32`, `usize`, etc) | `&PyLong` |
diff --git a/src/conversions/mod.rs b/src/conversions/mod.rs
new file mode 100644
index 00000000..a7ccff99
--- /dev/null
+++ b/src/conversions/mod.rs
@@ -0,0 +1,5 @@
+//! This module contains conversions between non-String Rust object and their string representation
+//! in Python
+
+mod osstr;
+mod path;
diff --git a/src/conversions/osstr.rs b/src/conversions/osstr.rs
new file mode 100644
index 00000000..be6f405b
--- /dev/null
+++ b/src/conversions/osstr.rs
@@ -0,0 +1,202 @@
+use crate::types::PyString;
+#[cfg(windows)]
+use crate::PyErr;
+use crate::PyNativeType;
+use crate::{
+    ffi, AsPyPointer, FromPyObject, IntoPy, PyAny, PyObject, PyResult, PyTryFrom, Python,
+    ToPyObject,
+};
+use std::borrow::Cow;
+use std::ffi::{OsStr, OsString};
+#[cfg(not(windows))]
+use std::os::raw::c_char;
+
+impl ToPyObject for OsStr {
+    fn to_object(&self, py: Python) -> PyObject {
+        // If the string is UTF-8, take the quick and easy shortcut
+        if let Some(valid_utf8_path) = self.to_str() {
+            return valid_utf8_path.to_object(py);
+        }
+
+        // All targets besides windows support the std::os::unix::ffi::OsStrExt API:
+        // https://doc.rust-lang.org/src/std/sys_common/mod.rs.html#59
+        #[cfg(not(windows))]
+        {
+            let bytes = std::os::unix::ffi::OsStrExt::as_bytes(self);
+
+            let ptr = bytes.as_ptr() as *const c_char;
+            let len = bytes.len() as ffi::Py_ssize_t;
+            unsafe {
+                // DecodeFSDefault automatically chooses an appropriate decoding mechanism to
+                // parse os strings losslessly (i.e. surrogateescape most of the time)
+                let pystring = ffi::PyUnicode_DecodeFSDefaultAndSize(ptr, len);
+                PyObject::from_owned_ptr(py, pystring)
+            }
+        }
+
+        #[cfg(windows)]
+        {
+            let wstr: Vec<u16> = std::os::windows::ffi::OsStrExt::encode_wide(self).collect();
+
+            unsafe {
+                // This will not panic because the data from encode_wide is well-formed Windows
+                // string data
+                PyObject::from_owned_ptr(
+                    py,
+                    ffi::PyUnicode_FromWideChar(wstr.as_ptr(), wstr.len() as ffi::Py_ssize_t),
+                )
+            }
+        }
+    }
+}
+
+// There's no FromPyObject implementation for &OsStr because albeit possible on Unix, this would
+// be impossible to implement on Windows. Hence it's omitted entirely
+
+impl FromPyObject<'_> for OsString {
+    fn extract(ob: &PyAny) -> PyResult<Self> {
+        let pystring = <PyString as PyTryFrom>::try_from(ob)?; // Cast PyAny to PyString
+
+        #[cfg(not(windows))]
+        {
+            // Decode from Python's lossless bytes string representation back into raw bytes
+            let fs_encoded_bytes = unsafe {
+                crate::Py::<crate::types::PyBytes>::from_owned_ptr(
+                    ob.py(),
+                    ffi::PyUnicode_EncodeFSDefault(pystring.as_ptr()),
+                )
+            };
+
+            // Create an OsStr view into the raw bytes from Python
+            let os_str: &OsStr = std::os::unix::ffi::OsStrExt::from_bytes(
+                fs_encoded_bytes.as_ref(ob.py()).as_bytes(),
+            );
+
+            Ok(os_str.to_os_string())
+        }
+
+        #[cfg(windows)]
+        {
+            // Take the quick and easy shortcut if UTF-8
+            if let Ok(utf8_string) = pystring.to_str() {
+                return Ok(utf8_string.to_owned().into());
+            }
+
+            // Get an owned allocated wide char buffer from PyString, which we have to deallocate
+            // ourselves
+            let size =
+                unsafe { ffi::PyUnicode_AsWideChar(pystring.as_ptr(), std::ptr::null_mut(), 0) };
+            if size == -1 {
+                return Err(PyErr::fetch(ob.py()));
+            }
+
+            let mut buffer = vec![0; size as usize];
+            let bytes_read =
+                unsafe { ffi::PyUnicode_AsWideChar(pystring.as_ptr(), buffer.as_mut_ptr(), size) };
+            assert_eq!(bytes_read, size);
+
+            // Copy wide char buffer into OsString
+            let os_string = std::os::windows::ffi::OsStringExt::from_wide(&buffer);
+
+            Ok(os_string)
+        }
+    }
+}
+
+impl IntoPy<PyObject> for &'_ OsStr {
+    #[inline]
+    fn into_py(self, py: Python) -> PyObject {
+        self.to_object(py)
+    }
+}
+
+impl ToPyObject for Cow<'_, OsStr> {
+    #[inline]
+    fn to_object(&self, py: Python) -> PyObject {
+        (&self as &OsStr).to_object(py)
+    }
+}
+
+impl IntoPy<PyObject> for Cow<'_, OsStr> {
+    #[inline]
+    fn into_py(self, py: Python) -> PyObject {
+        self.to_object(py)
+    }
+}
+
+impl ToPyObject for OsString {
+    #[inline]
+    fn to_object(&self, py: Python) -> PyObject {
+        (&self as &OsStr).to_object(py)
+    }
+}
+
+impl IntoPy<PyObject> for OsString {
+    fn into_py(self, py: Python) -> PyObject {
+        self.to_object(py)
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use crate::{types::PyString, IntoPy, PyObject, Python, ToPyObject};
+    use std::fmt::Debug;
+    use std::{
+        borrow::Cow,
+        ffi::{OsStr, OsString},
+    };
+
+    #[test]
+    #[cfg(not(windows))]
+    fn test_non_utf8_conversion() {
+        Python::with_gil(|py| {
+            use std::os::unix::ffi::OsStrExt;
+
+            // this is not valid UTF-8
+            let payload = &[250, 251, 252, 253, 254, 255, 0, 255];
+            let os_str = OsStr::from_bytes(payload);
+
+            // do a roundtrip into Pythonland and back and compare
+            let py_str: PyObject = os_str.into_py(py);
+            let os_str_2: OsString = py_str.extract(py).unwrap();
+            assert_eq!(os_str, os_str_2);
+        });
+    }
+
+    #[test]
+    fn test_topyobject_roundtrip() {
+        Python::with_gil(|py| {
+            fn test_roundtrip<T: ToPyObject + AsRef<OsStr> + Debug>(py: Python, obj: T) {
+                let pyobject = obj.to_object(py);
+                let pystring: &PyString = pyobject.extract(py).unwrap();
+                assert_eq!(pystring.to_string_lossy(), obj.as_ref().to_string_lossy());
+                let roundtripped_obj: OsString = pystring.extract().unwrap();
+                assert_eq!(obj.as_ref(), roundtripped_obj.as_os_str());
+            }
+            let os_str = OsStr::new("Hello\0\n🐍");
+            test_roundtrip::<&OsStr>(py, os_str);
+            test_roundtrip::<Cow<'_, OsStr>>(py, Cow::Borrowed(os_str));
+            test_roundtrip::<Cow<'_, OsStr>>(py, Cow::Owned(os_str.to_os_string()));
+            test_roundtrip::<OsString>(py, os_str.to_os_string());
+        });
+    }
+
+    #[test]
+    fn test_intopy_roundtrip() {
+        Python::with_gil(|py| {
+            fn test_roundtrip<T: IntoPy<PyObject> + AsRef<OsStr> + Debug + Clone>(
+                py: Python,
+                obj: T,
+            ) {
+                let pyobject = obj.clone().into_py(py);
+                let pystring: &PyString = pyobject.extract(py).unwrap();
+                assert_eq!(pystring.to_string_lossy(), obj.as_ref().to_string_lossy());
+                let roundtripped_obj: OsString = pystring.extract().unwrap();
+                assert!(obj.as_ref() == roundtripped_obj.as_os_str());
+            }
+            let os_str = OsStr::new("Hello\0\n🐍");
+            test_roundtrip::<&OsStr>(py, os_str);
+            test_roundtrip::<OsString>(py, os_str.to_os_string());
+        })
+    }
+}
diff --git a/src/conversions/path.rs b/src/conversions/path.rs
new file mode 100644
index 00000000..a08345b9
--- /dev/null
+++ b/src/conversions/path.rs
@@ -0,0 +1,115 @@
+use crate::{FromPyObject, IntoPy, PyAny, PyObject, PyResult, Python, ToPyObject};
+use std::borrow::Cow;
+use std::ffi::OsString;
+use std::path::{Path, PathBuf};
+
+impl ToPyObject for Path {
+    fn to_object(&self, py: Python) -> PyObject {
+        self.as_os_str().to_object(py)
+    }
+}
+
+// See osstr.rs for why there's no FromPyObject impl for &Path
+
+impl FromPyObject<'_> for PathBuf {
+    fn extract(ob: &PyAny) -> PyResult<Self> {
+        Ok(PathBuf::from(OsString::extract(ob)?))
+    }
+}
+
+impl<'a> IntoPy<PyObject> for &'a Path {
+    #[inline]
+    fn into_py(self, py: Python) -> PyObject {
+        self.as_os_str().to_object(py)
+    }
+}
+
+impl<'a> ToPyObject for Cow<'a, Path> {
+    #[inline]
+    fn to_object(&self, py: Python) -> PyObject {
+        self.as_os_str().to_object(py)
+    }
+}
+
+impl<'a> IntoPy<PyObject> for Cow<'a, Path> {
+    #[inline]
+    fn into_py(self, py: Python) -> PyObject {
+        self.to_object(py)
+    }
+}
+
+impl ToPyObject for PathBuf {
+    #[inline]
+    fn to_object(&self, py: Python) -> PyObject {
+        self.as_os_str().to_object(py)
+    }
+}
+
+impl IntoPy<PyObject> for PathBuf {
+    fn into_py(self, py: Python) -> PyObject {
+        self.into_os_string().to_object(py)
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use crate::{types::PyString, IntoPy, PyObject, Python, ToPyObject};
+    use std::borrow::Cow;
+    use std::fmt::Debug;
+    use std::path::{Path, PathBuf};
+
+    #[test]
+    #[cfg(not(windows))]
+    fn test_non_utf8_conversion() {
+        Python::with_gil(|py| {
+            use std::ffi::OsStr;
+            use std::os::unix::ffi::OsStrExt;
+
+            // this is not valid UTF-8
+            let payload = &[250, 251, 252, 253, 254, 255, 0, 255];
+            let path = Path::new(OsStr::from_bytes(payload));
+
+            // do a roundtrip into Pythonland and back and compare
+            let py_str: PyObject = path.into_py(py);
+            let path_2: PathBuf = py_str.extract(py).unwrap();
+            assert_eq!(path, path_2);
+        });
+    }
+
+    #[test]
+    fn test_topyobject_roundtrip() {
+        Python::with_gil(|py| {
+            fn test_roundtrip<T: ToPyObject + AsRef<Path> + Debug>(py: Python, obj: T) {
+                let pyobject = obj.to_object(py);
+                let pystring: &PyString = pyobject.extract(py).unwrap();
+                assert_eq!(pystring.to_string_lossy(), obj.as_ref().to_string_lossy());
+                let roundtripped_obj: PathBuf = pystring.extract().unwrap();
+                assert_eq!(obj.as_ref(), roundtripped_obj.as_path());
+            }
+            let path = Path::new("Hello\0\n🐍");
+            test_roundtrip::<&Path>(py, path);
+            test_roundtrip::<Cow<'_, Path>>(py, Cow::Borrowed(path));
+            test_roundtrip::<Cow<'_, Path>>(py, Cow::Owned(path.to_path_buf()));
+            test_roundtrip::<PathBuf>(py, path.to_path_buf());
+        });
+    }
+
+    #[test]
+    fn test_intopy_roundtrip() {
+        Python::with_gil(|py| {
+            fn test_roundtrip<T: IntoPy<PyObject> + AsRef<Path> + Debug + Clone>(
+                py: Python,
+                obj: T,
+            ) {
+                let pyobject = obj.clone().into_py(py);
+                let pystring: &PyString = pyobject.extract(py).unwrap();
+                assert_eq!(pystring.to_string_lossy(), obj.as_ref().to_string_lossy());
+                let roundtripped_obj: PathBuf = pystring.extract().unwrap();
+                assert!(obj.as_ref() == roundtripped_obj.as_path());
+            }
+            let path = Path::new("Hello\0\n🐍");
+            test_roundtrip::<&Path>(py, path);
+            test_roundtrip::<PathBuf>(py, path.to_path_buf());
+        })
+    }
+}
diff --git a/src/lib.rs b/src/lib.rs
index ccbd0e67..874b0562 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -180,6 +180,7 @@ pub mod buffer;
 pub mod callback;
 pub mod class;
 pub mod conversion;
+mod conversions;
 #[macro_use]
 #[doc(hidden)]
 pub mod derive_utils;
diff --git a/src/types/string.rs b/src/types/string.rs
index 18b05c99..7e75556e 100644
--- a/src/types/string.rs
+++ b/src/types/string.rs
@@ -131,6 +131,13 @@ impl<'a> ToPyObject for Cow<'a, str> {
     }
 }
 
+impl IntoPy<PyObject> for Cow<'_, str> {
+    #[inline]
+    fn into_py(self, py: Python) -> PyObject {
+        self.to_object(py)
+    }
+}
+
 /// Converts a Rust `String` to a Python object.
 /// See `PyString::new` for details on the conversion.
 impl ToPyObject for String {