Welcome to Western Sky Vacation Homes Property Managment

In Memoriam

Matthew M. McCaskell, aged 37, owner of Western Sky Vacation Homes, LLC and lifelong Black Hills resident, passed away on September 3, 2026, after a battle with stomach cancer. He was beloved by family and friends. Matt always enjoyed interacting with his guests and helping them to create lasting memories. He always had a positive attitude, a big smile, and a friendly greeting for everyone he met. He will be dearly missed.

Mickelson Trail Lodging owner and Matt’s dad, Larry McCaskell, will be taking over management of the cabins.