diff --git a/docs/API.md b/docs/API.md
index 88d43d57..0a9a1949 100644
--- a/docs/API.md
+++ b/docs/API.md
@@ -47,6 +47,7 @@ inputProps | object | {} | Props to be applied directly to the input. `onBlur`,
 isInvalid | boolean | false | Adds the `is-invalid` classname to the `form-control`. Only affects Bootstrap 4.
 isLoading | boolean | false | Indicate whether an asynchronous data fetch is happening.
 isValid | boolean | false | Adds the `is-valid` classname to the `form-control`. Only affects Bootstrap 4.
+keepOpen | boolean \| function | `false` | Allows selecting of multiple values from the menu at once.
 labelKey | string \| function | `'label'` | See full documentation in the [Rendering section](Rendering.md#labelkey-string--function).
 onChange | function | | Invoked when the set of selections changes (ie: an item is added or removed). For consistency, `selected` is always an array of selections, even if multi-selection is not enabled. <br><br><pre>`(selected: Array<Object\|string>) => void`</pre>
 onInputChange | function | | Invoked when the input value changes. Receives the string value of the input (`text`), as well as the original event. <br><br><pre>`(text: string, event: Event) => void`</pre>
diff --git a/src/components/Typeahead/Typeahead.stories.tsx b/src/components/Typeahead/Typeahead.stories.tsx
index 4fc4765d..e7a2f84d 100644
--- a/src/components/Typeahead/Typeahead.stories.tsx
+++ b/src/components/Typeahead/Typeahead.stories.tsx
@@ -95,6 +95,13 @@ AllowNew.args = {
   allowNew: true,
 };
 
+export const KeepOpen = Template.bind({});
+KeepOpen.args = {
+  ...defaultProps,
+  multiple: true,
+  keepOpen: true,
+};
+
 export const CustomInput = Template.bind({});
 CustomInput.args = {
   ...defaultProps,
diff --git a/src/components/Typeahead/Typeahead.test.tsx b/src/components/Typeahead/Typeahead.test.tsx
index 03e4cb0c..2f6d0c4d 100644
--- a/src/components/Typeahead/Typeahead.test.tsx
+++ b/src/components/Typeahead/Typeahead.test.tsx
@@ -1,4 +1,4 @@
-import React, { createRef, forwardRef } from 'react';
+import React, { createRef, forwardRef, useState } from 'react';
 
 import TypeaheadComponent, { TypeaheadComponentProps } from './Typeahead';
 import Typeahead, {
@@ -30,6 +30,7 @@ import {
 } from '../../tests/helpers';
 
 import states from '../../tests/data';
+import { Option } from '../../types';
 
 const ID = 'rbt-id';
 
@@ -1202,6 +1203,96 @@ describe('<Typeahead>', () => {
       expect(items[0]).toHaveTextContent(`${newSelectionPrefix}${value}`);
     });
   });
+
+  describe('keepOpen behaviour', () => {
+    it('should not affect single selection mode', async () => {
+      const user = userEvent.setup();
+      render(<Default />);
+      getInput().focus();
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(menu).not.toBeInTheDocument();
+    });
+
+    it('should default to false', async () => {
+      const user = userEvent.setup();
+      render(<MultiSelect selected={[]} />);
+      getInput().focus();
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(menu).not.toBeInTheDocument();
+    });
+
+    it('should keep the menu open after selection', async () => {
+      const user = userEvent.setup();
+      render(<MultiSelect selected={[]} keepOpen />);
+      getInput().focus();
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(menu).toBeInTheDocument();
+    });
+
+    it('should close the menu if keepOpen function returns false', async () => {
+      const user = userEvent.setup();
+      const ctrlPressed = false;
+      render(<MultiSelect selected={[]} keepOpen={() => ctrlPressed} />);
+      getInput().focus();
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(menu).not.toBeInTheDocument();
+    });
+
+    it('should keep the menu open if keepOpen function returns true', async () => {
+      const user = userEvent.setup();
+      const ctrlPressed = true;
+      render(<MultiSelect selected={[]} keepOpen={() => ctrlPressed} />);
+      getInput().focus();
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(menu).toBeInTheDocument();
+    });
+
+    it('should retain the search input after selection', async () => {
+      const user = userEvent.setup();
+      render(<MultiSelect selected={[]} keepOpen />);
+
+      const search = 'Ala';
+      const input = getInput();
+      await user.type(input, search);
+
+      const menu = await findMenu();
+      expect(menu).toBeInTheDocument();
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(input).toHaveValue(search);
+    });
+
+    it('should reset hint and active item after selection', async () => {
+      const user = userEvent.setup();
+      const KeepOpenAndSelect = () => {
+        const [selected, setSelected] = useState<Option[]>([]);
+        return (
+          <MultiSelect selected={selected} onChange={setSelected} keepOpen />
+        );
+      };
+
+      const { container } = render(<KeepOpenAndSelect />);
+
+      const input = getInput();
+      const hint = getHint(container);
+
+      await user.type(input, 'Ala');
+      expect(input).toHaveFocus();
+      expect(hint).toHaveValue('Alabama');
+
+      await user.keyboard('{ArrowDown}{Enter}');
+      expect(hint).toHaveValue('Alaska');
+    });
+  });
 });
 
 describe('<Typeahead> Public Methods', () => {
diff --git a/src/components/Typeahead/__snapshots__/Typeahead.test.tsx.snap b/src/components/Typeahead/__snapshots__/Typeahead.test.tsx.snap
index d4ce1a9c..fc556093 100644
--- a/src/components/Typeahead/__snapshots__/Typeahead.test.tsx.snap
+++ b/src/components/Typeahead/__snapshots__/Typeahead.test.tsx.snap
@@ -475,6 +475,88 @@ exports[`<Typeahead> InputGrouping story renders snapshot 1`] = `
 </div>
 `;
 
+exports[`<Typeahead> KeepOpen story renders snapshot 1`] = `
+<div
+  className="rbt"
+  style={
+    Object {
+      "outline": "none",
+      "position": "relative",
+    }
+  }
+  tabIndex={-1}
+>
+  <div
+    className="rbt-input-multi form-control rbt-input"
+    onClick={[Function]}
+    onFocus={[Function]}
+    tabIndex={-1}
+  >
+    <div
+      className="rbt-input-wrapper"
+    >
+      <div
+        style={
+          Object {
+            "display": "flex",
+            "flex": 1,
+            "height": "100%",
+            "position": "relative",
+          }
+        }
+      >
+        <input
+          aria-autocomplete="list"
+          aria-haspopup="listbox"
+          autoComplete="off"
+          className="rbt-input-main"
+          onBlur={[Function]}
+          onChange={[Function]}
+          onClick={[Function]}
+          onFocus={[Function]}
+          onKeyDown={[Function]}
+          placeholder="Choose a state..."
+          style={
+            Object {
+              "backgroundColor": "transparent",
+              "border": 0,
+              "boxShadow": "none",
+              "cursor": "inherit",
+              "outline": "none",
+              "padding": 0,
+              "width": "100%",
+              "zIndex": 1,
+            }
+          }
+          type="text"
+          value=""
+        />
+        <input
+          aria-hidden={true}
+          className="rbt-input-hint"
+          readOnly={true}
+          style={
+            Object {
+              "backgroundColor": "transparent",
+              "borderColor": "transparent",
+              "boxShadow": "none",
+              "color": "rgba(0, 0, 0, 0.54)",
+              "left": 0,
+              "pointerEvents": "none",
+              "position": "absolute",
+              "top": 0,
+              "width": "100%",
+            }
+          }
+          tabIndex={-1}
+          value=""
+        />
+      </div>
+    </div>
+  </div>
+</div>
+`;
+
 exports[`<Typeahead> LoadingState story renders snapshot 1`] = `
 <div
   className="rbt has-aux"
diff --git a/src/core/Typeahead.tsx b/src/core/Typeahead.tsx
index 35a7e0b8..004b7e22 100644
--- a/src/core/Typeahead.tsx
+++ b/src/core/Typeahead.tsx
@@ -43,6 +43,7 @@ import { DEFAULT_LABELKEY } from '../constants';
 
 import type {
   FilterByCallback,
+  KeepOpen,
   Option,
   RefElement,
   SelectEvent,
@@ -109,6 +110,11 @@ const propTypes = {
    * Whether the filter should ignore accents and other diacritical marks.
    */
   ignoreDiacritics: checkPropType(PropTypes.bool, ignoreDiacriticsType),
+  /**
+   * Whether the menu should stay open after selecting an item.
+   * Can be used allow selecting multiple items at once.
+   */
+  keepOpen: PropTypes.oneOfType([PropTypes.bool, PropTypes.func]),
   /**
    * Specify the option key to use for display or a function returning the
    * display string. By default, the selector will use the `label` key.
@@ -194,6 +200,7 @@ const defaultProps = {
   filterBy: [],
   highlightOnlyResult: false,
   ignoreDiacritics: true,
+  keepOpen: false,
   labelKey: DEFAULT_LABELKEY,
   maxResults: 100,
   minLength: 0,
@@ -296,6 +303,14 @@ function triggerInputChange(input: HTMLInputElement, value: string) {
   input.dispatchEvent(e);
 }
 
+function shouldKeepOpen(keepOpen: KeepOpen = false): boolean {
+  if (typeof keepOpen === 'function') {
+    return keepOpen();
+  }
+
+  return keepOpen;
+}
+
 class Typeahead extends React.Component<Props, TypeaheadState> {
   static propTypes = propTypes;
   static defaultProps = defaultProps;
@@ -574,7 +589,7 @@ class Typeahead extends React.Component<Props, TypeaheadState> {
   };
 
   _handleSelectionAdd = (option: Option) => {
-    const { multiple, labelKey } = this.props;
+    const { keepOpen, labelKey, multiple } = this.props;
 
     let selected: Option[];
     let selection = option;
@@ -599,12 +614,24 @@ class Typeahead extends React.Component<Props, TypeaheadState> {
     }
 
     this.setState(
-      (state, props) => ({
-        ...hideMenu(state, props),
-        initialItem: selection,
-        selected,
-        text,
-      }),
+      (state, props) => {
+        if (multiple && shouldKeepOpen(keepOpen)) {
+          return {
+            ...state,
+            activeIndex: -1,
+            activeItem: undefined,
+            initialItem: selection,
+            selected,
+          };
+        }
+
+        return {
+          ...hideMenu(state, props),
+          initialItem: selection,
+          selected,
+          text,
+        };
+      },
       () => this._handleChange(selected)
     );
   };
diff --git a/src/types.ts b/src/types.ts
index 8bab27bb..c2af3f90 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -25,6 +25,8 @@ export type FilterByCallback = (
 
 export type Id = string;
 
+export type KeepOpen = boolean | (() => boolean);
+
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 export type Option = string | Record<string, any>;
 
@@ -82,6 +84,7 @@ export interface TypeaheadProps {
   id?: Id;
   ignoreDiacritics: boolean;
   inputProps?: InputProps;
+  keepOpen?: KeepOpen;
   labelKey: LabelKey;
   maxResults: number;
   minLength: number;