diff --git a/README.md b/README.md
index e98e89cf..aef3f25d 100644
--- a/README.md
+++ b/README.md
@@ -639,7 +639,8 @@ The `file` is resolved relative to the current working directory. If an `extends
 key is present once read, its value will be resolved as a path relative to `file`
 and loaded recursively. Settings from a file referenced by `extends` are applied
 first, then those of `file` are applied on top (overriding any of the same keys
-appearing in the referenced file).
+appearing in the referenced file). If either the `file` or `extends` path begins
+with the `~` directory, it will act as a placeholder for the home directory.
 
 #### parsers
 
diff --git a/demo/markdownlint-browser.js b/demo/markdownlint-browser.js
index 124f252e..066d9f18 100644
--- a/demo/markdownlint-browser.js
+++ b/demo/markdownlint-browser.js
@@ -995,6 +995,18 @@ function deepFreeze(obj) {
     return obj;
 }
 module.exports.deepFreeze = deepFreeze;
+/**
+ * Expands a path with a tilde to an absolute path.
+ *
+ * @param {string} file Path that may begin with a tilde.
+ * @param {Object} os Node.js "os" module.
+ * @returns {string} Absolute path (or original path).
+ */
+function expandTildePath(file, os) {
+    var homedir = os && os.homedir();
+    return homedir ? file.replace(/^~($|\/|\\)/, "".concat(homedir, "$1")) : file;
+}
+module.exports.expandTildePath = expandTildePath;
 
 
 /***/ }),
@@ -1030,6 +1042,16 @@ module.exports = markdownit;
 
 /***/ }),
 
+/***/ "?a32b":
+/*!********************!*\
+  !*** os (ignored) ***!
+  \********************/
+/***/ (() => {
+
+/* (ignored) */
+
+/***/ }),
+
 /***/ "?b85c":
 /*!**********************!*\
   !*** path (ignored) ***!
@@ -2070,6 +2092,8 @@ function readConfig(file, parsers, fs, callback) {
         fs = __webpack_require__(/*! fs */ "?ec0a");
     }
     // Read file
+    var os = __webpack_require__(/*! os */ "?a32b");
+    file = helpers.expandTildePath(file, os);
     fs.readFile(file, "utf8", function (err, content) {
         if (err) {
             return callback(err);
@@ -2084,7 +2108,7 @@ function readConfig(file, parsers, fs, callback) {
         var configExtends = config.extends;
         if (configExtends) {
             delete config.extends;
-            return resolveConfigExtends(file, configExtends, fs, function (_, resolvedExtends) { return readConfig(resolvedExtends, parsers, fs, function (errr, extendsConfig) {
+            return resolveConfigExtends(file, helpers.expandTildePath(configExtends, os), fs, function (_, resolvedExtends) { return readConfig(resolvedExtends, parsers, fs, function (errr, extendsConfig) {
                 if (errr) {
                     return callback(errr);
                 }
@@ -2121,6 +2145,8 @@ function readConfigSync(file, parsers, fs) {
         fs = __webpack_require__(/*! fs */ "?ec0a");
     }
     // Read file
+    var os = __webpack_require__(/*! os */ "?a32b");
+    file = helpers.expandTildePath(file, os);
     var content = fs.readFileSync(file, "utf8");
     // Try to parse file
     var _a = parseConfiguration(file, content, parsers), config = _a.config, message = _a.message;
@@ -2131,7 +2157,7 @@ function readConfigSync(file, parsers, fs) {
     var configExtends = config.extends;
     if (configExtends) {
         delete config.extends;
-        var resolvedExtends = resolveConfigExtendsSync(file, configExtends, fs);
+        var resolvedExtends = resolveConfigExtendsSync(file, helpers.expandTildePath(configExtends, os), fs);
         return __assign(__assign({}, readConfigSync(resolvedExtends, parsers, fs)), config);
     }
     return config;
diff --git a/helpers/helpers.js b/helpers/helpers.js
index 07683116..249830dd 100644
--- a/helpers/helpers.js
+++ b/helpers/helpers.js
@@ -1021,3 +1021,16 @@ function deepFreeze(obj) {
   return obj;
 }
 module.exports.deepFreeze = deepFreeze;
+
+/**
+ * Expands a path with a tilde to an absolute path.
+ *
+ * @param {string} file Path that may begin with a tilde.
+ * @param {Object} os Node.js "os" module.
+ * @returns {string} Absolute path (or original path).
+ */
+function expandTildePath(file, os) {
+  const homedir = os && os.homedir();
+  return homedir ? file.replace(/^~($|\/|\\)/, `${homedir}$1`) : file;
+}
+module.exports.expandTildePath = expandTildePath;
diff --git a/lib/markdownlint.js b/lib/markdownlint.js
index 224e1f42..15976d0e 100644
--- a/lib/markdownlint.js
+++ b/lib/markdownlint.js
@@ -1026,6 +1026,8 @@ function readConfig(file, parsers, fs, callback) {
     fs = require("fs");
   }
   // Read file
+  const os = require("os");
+  file = helpers.expandTildePath(file, os);
   fs.readFile(file, "utf8", (err, content) => {
     if (err) {
       return callback(err);
@@ -1042,7 +1044,7 @@ function readConfig(file, parsers, fs, callback) {
       delete config.extends;
       return resolveConfigExtends(
         file,
-        configExtends,
+        helpers.expandTildePath(configExtends, os),
         fs,
         (_, resolvedExtends) => readConfig(
           resolvedExtends,
@@ -1093,6 +1095,8 @@ function readConfigSync(file, parsers, fs) {
     fs = require("fs");
   }
   // Read file
+  const os = require("os");
+  file = helpers.expandTildePath(file, os);
   const content = fs.readFileSync(file, "utf8");
   // Try to parse file
   const { config, message } = parseConfiguration(file, content, parsers);
@@ -1103,7 +1107,11 @@ function readConfigSync(file, parsers, fs) {
   const configExtends = config.extends;
   if (configExtends) {
     delete config.extends;
-    const resolvedExtends = resolveConfigExtendsSync(file, configExtends, fs);
+    const resolvedExtends = resolveConfigExtendsSync(
+      file,
+      helpers.expandTildePath(configExtends, os),
+      fs
+    );
     return {
       ...readConfigSync(resolvedExtends, parsers, fs),
       ...config
diff --git a/test/markdownlint-test-config.js b/test/markdownlint-test-config.js
index 6c88ed5a..8a7de80b 100644
--- a/test/markdownlint-test-config.js
+++ b/test/markdownlint-test-config.js
@@ -2,10 +2,13 @@
 
 "use strict";
 
+const os = require("os");
 const path = require("path");
 const test = require("ava").default;
 const markdownlint = require("../lib/markdownlint");
 
+const sameFileSystem = (path.relative(os.homedir(), __dirname) !== __dirname);
+
 test.cb("configSingle", (t) => {
   t.plan(2);
   markdownlint.readConfig("./test/config/config-child.json",
@@ -28,6 +31,20 @@ test.cb("configAbsolute", (t) => {
     });
 });
 
+if (sameFileSystem) {
+  test.cb("configTilde", (t) => {
+    t.plan(2);
+    markdownlint.readConfig(
+      `~/${path.relative(os.homedir(), "./test/config/config-child.json")}`,
+      function callback(err, actual) {
+        t.falsy(err);
+        const expected = require("./config/config-child.json");
+        t.deepEqual(actual, expected, "Config object not correct.");
+        t.end();
+      });
+  });
+}
+
 test.cb("configMultiple", (t) => {
   t.plan(2);
   markdownlint.readConfig("./test/config/config-grandparent.json",
@@ -60,9 +77,10 @@ test.cb("configMultipleWithRequireResolve", (t) => {
 });
 
 test.cb("configCustomFileSystem", (t) => {
-  t.plan(5);
-  const file = path.resolve("/dir/file.json");
-  const extended = path.resolve("/dir/extended.json");
+  t.plan(3);
+  const file = "/dir/file.json";
+  const extended = "~/dir/extended.json";
+  const expanded = path.join(os.homedir(), extended.slice(1));
   const fileContent = {
     "extends": extended,
     "default": true,
@@ -74,20 +92,16 @@ test.cb("configCustomFileSystem", (t) => {
   };
   const fsApi = {
     "access": (p, m, cb) => {
-      t.is(p, extended);
+      t.is(p, expanded);
       return (cb || m)();
     },
     "readFile": (p, o, cb) => {
-      switch (p) {
-        case file:
-          t.is(p, file);
-          return cb(null, JSON.stringify(fileContent));
-        case extended:
-          t.is(p, extended);
-          return cb(null, JSON.stringify(extendedContent));
-        default:
-          return t.fail();
+      if (p === file) {
+        return cb(null, JSON.stringify(fileContent));
+      } else if (p === expanded) {
+        return cb(null, JSON.stringify(extendedContent));
       }
+      return t.fail(p);
     }
   };
   markdownlint.readConfig(
@@ -254,6 +268,16 @@ test("configAbsoluteSync", (t) => {
   t.deepEqual(actual, expected, "Config object not correct.");
 });
 
+if (sameFileSystem) {
+  test("configTildeSync", (t) => {
+    t.plan(1);
+    const actual = markdownlint.readConfigSync(
+      `~/${path.relative(os.homedir(), "./test/config/config-child.json")}`);
+    const expected = require("./config/config-child.json");
+    t.deepEqual(actual, expected, "Config object not correct.");
+  });
+}
+
 test("configMultipleSync", (t) => {
   t.plan(1);
   const actual =
@@ -362,9 +386,10 @@ test("configMultipleHybridSync", (t) => {
 });
 
 test("configCustomFileSystemSync", (t) => {
-  t.plan(4);
-  const file = path.resolve("/dir/file.json");
-  const extended = path.resolve("/dir/extended.json");
+  t.plan(2);
+  const file = "/dir/file.json";
+  const extended = "~/dir/extended.json";
+  const expanded = path.join(os.homedir(), extended.slice(1));
   const fileContent = {
     "extends": extended,
     "default": true,
@@ -376,19 +401,15 @@ test("configCustomFileSystemSync", (t) => {
   };
   const fsApi = {
     "accessSync": (p) => {
-      t.is(p, extended);
+      t.is(p, expanded);
     },
     "readFileSync": (p) => {
-      switch (p) {
-        case file:
-          t.is(p, file);
-          return JSON.stringify(fileContent);
-        case extended:
-          t.is(p, extended);
-          return JSON.stringify(extendedContent);
-        default:
-          return t.fail();
+      if (p === file) {
+        return JSON.stringify(fileContent);
+      } else if (p === expanded) {
+        return JSON.stringify(extendedContent);
       }
+      return t.fail(p);
     }
   };
   const actual = markdownlint.readConfigSync(file, null, fsApi);
diff --git a/test/markdownlint-test-helpers.js b/test/markdownlint-test-helpers.js
index 8bad7e65..4d7c70a0 100644
--- a/test/markdownlint-test-helpers.js
+++ b/test/markdownlint-test-helpers.js
@@ -2,6 +2,8 @@
 
 "use strict";
 
+const os = require("os");
+const path = require("path");
 const test = require("ava").default;
 const helpers = require("../helpers");
 
@@ -1303,3 +1305,33 @@ test("htmlElementRanges", (t) => {
   const actual = helpers.htmlElementRanges(params, lineMetadata);
   t.deepEqual(actual, expected);
 });
+
+test("expandTildePath", (t) => {
+  t.plan(16);
+  const homedir = os.homedir();
+  t.is(helpers.expandTildePath("", os), "");
+  t.is(helpers.expandTildePath("", null), "");
+  t.is(
+    path.resolve(helpers.expandTildePath("~", os)),
+    homedir
+  );
+  t.is(helpers.expandTildePath("~", null), "~");
+  t.is(helpers.expandTildePath("file", os), "file");
+  t.is(helpers.expandTildePath("file", null), "file");
+  t.is(helpers.expandTildePath("/file", os), "/file");
+  t.is(helpers.expandTildePath("/file", null), "/file");
+  t.is(
+    path.resolve(helpers.expandTildePath("~/file", os)),
+    path.join(homedir, "/file")
+  );
+  t.is(helpers.expandTildePath("~/file", null), "~/file");
+  t.is(helpers.expandTildePath("dir/file", os), "dir/file");
+  t.is(helpers.expandTildePath("dir/file", null), "dir/file");
+  t.is(helpers.expandTildePath("/dir/file", os), "/dir/file");
+  t.is(helpers.expandTildePath("/dir/file", null), "/dir/file");
+  t.is(
+    path.resolve(helpers.expandTildePath("~/dir/file", os)),
+    path.join(homedir, "/dir/file")
+  );
+  t.is(helpers.expandTildePath("~/dir/file", null), "~/dir/file");
+});