diff --git a/src/poetry/core/vcs/git.py b/src/poetry/core/vcs/git.py
index 28f1fd28c..cae85729f 100644
--- a/src/poetry/core/vcs/git.py
+++ b/src/poetry/core/vcs/git.py
@@ -14,7 +14,7 @@
 USER = r"[a-zA-Z0-9_.-]+"
 RESOURCE = r"[a-zA-Z0-9_.-]+"
 PORT = r"\d+"
-PATH = r"[\w~.\-/\\]+"
+PATH = r"[\w~.\-/\\\$]+"
 NAME = r"[\w~.\-]+"
 REV = r"[^@#]+?"
 SUBDIR = r"[\w\-/\\]+"
diff --git a/tests/vcs/test_vcs.py b/tests/vcs/test_vcs.py
index cf7563a6b..3c18b54c1 100644
--- a/tests/vcs/test_vcs.py
+++ b/tests/vcs/test_vcs.py
@@ -86,6 +86,12 @@
             "git+file://C:\\Users\\hello\\testing.git#zkat/windows-files",
             GitUrl("file://C:\\Users\\hello\\testing.git", "zkat/windows-files", None),
         ),
+        # hidden directories on Windows ues $ in their path
+        # python-poetry/poetry#5493
+        (
+            "git+file://C:\\Users\\hello$\\testing.git#zkat/windows-files",
+            GitUrl("file://C:\\Users\\hello$\\testing.git", "zkat/windows-files", None),
+        ),
         (
             "git+https://git.example.com/sdispater/project/my_repo.git",
             GitUrl("https://git.example.com/sdispater/project/my_repo.git", None, None),