Håkan Wennerberg

This widget requires WordPress 3.5 or newer.
Primary features of HW Image Widget:
<ul>
<li>Allow you to choose responsive or fixed behavior.</li>
<li>Fixed sized images allow you to define width/height with, or without kept aspect ratio.</li>
<li>Responsive sized images will allow you to define “fill width” or not.</li>
<li>Uses TinyMCE for rich text editing of the image text field.</li>
<li>Allow you to create a custom widget HTML-template in the active theme to override the default layout.</li>
<li>Default settings can be overridden using filter.</li>
<li>Works with Carrington Build.</li>
<li>Works with the theme customizer.</li>
<li>Available in English and Swedish.</li>
</ul>
For more info, visit http://webartisan.se/hw-image-widget/

HW Image Widget

Image widget that will allow you to choose responsive or fixed sized behavior. Includes TinyMCE rich text editing of the text description.

CrestaProject

Cresta Image In Widget it’s a widget that allows you to simply add an image in a widget, choose the size, choose the border radius, add a link on it and add text under the image.
Some features
<ul>
<li>Add an image in the widget</li>
<li>Choose the image size</li>
<li>Add a border radius at the image</li>
<li>Choose where to show the widget (entire website, only home page, only all posts, etc…)</li>
<li>Add a link on the image</li>
<li>Add text under the image</li>
</ul>
This plugin can be useful if you want to show an “About Me” section in your sidebar, or the logo of your company in your footer, or for any reason you need an image in the widget. 
All features are optional so you can choose what to show in your website and what not!

Cresta Image In Widget

Simple plugin to show an image, photo or logo in a widget with text and link

HW Image Widget vs Cresta Image In Widget