The first Toolleen Hotel was a timber structure brought from Graytown in 1871. In 1873 it was replaced by the Plough Inn and included a general store. A grander brick hotel was built in 1905 but this was destroyed by fire in 1926 and replaced with the current hotel.
The Tin Shed was originally built in 1908 to house the horses and coaches that stopped to rest at the hotel. It is now used as an entertainment venue.