The Chesapeake Bay Retriever was developed to hunt waterfowl under adverse conditions, facing strong tides in rough water, high winds and sometimes even having to break through ice. It is an extraordinary swimmer, with a strong, yet tender, bite enabling it to carry birds. It has powerful limbs and webbed feet. The Chessie is slightly longer than tall, with its hindquarters as high, or higher, than its forequarters. Its coat is rendered virtually waterproof by virtue of its oily, harsh outer coat and dense wooly undercoat. The color matches its working surroundings: any shade of brown, sedge or dead grass.

The Chesapeake Bay Retriever is hardy enough to not only withstand, but also relish, repeated plunges into icy water. It loves to swim and retrieve. Despite an active life when outdoors, inside it tends to be calm. The Chessie tends to be independent, although it is eager to learn. It is reserved with strangers and can be protective; it also can be aggressive toward strange dogs if challenged. This is the hardiest, most strong-willed and protective of the retriever breeds.