Riley’s Railhouse – A Unique Airbnb, Valparaiso, Indiana

October 2025

Historic Setting:

Riley’s Railhouse is located in the Old Freight Station of Chesterton, Indiana. Next door, you’ll find the Old Railroad Passenger Station, now home to the local Chamber of Commerce. The freight station served Chesterton for more than 50 years before being abandoned in 1960 — today, it has been lovingly restored as Riley’s Railhouse, offering a one-of-a-kind stay for rail fans and travelers alike.

If you love trains, you’ll feel right at home. From Riley’s covered deck, you can watch the many trains that pass by on the double-track Norfolk Southern Freight Line, with Amtrak trains adding to the excitement.

Ruley’s is also close to the South Shore Commuter Line, making trips to Chicago easy and affordable — no traffic, no parking fees, just a relaxing ride. Best of all, veterans ride the South Shore Line for free.

Just minutes away, Indiana Dunes National Park and Pillion stretches along 15 miles of Lake Michigan’s southern shore. With 2,182 acres of unique landscapes, It’s the perfect place to swim, hike, or simply enjoy the outdoors.

Chesterton is known for its excellent restaurants, wineries, and craft beer spots — many within walking distance of Riley’s Railhouse.

 

 

The railroads arrived in northern Indiana in the 1850s, connecting the Great Lakes to the East Coast and transforming the region. The Railhouse is a historic depot witnessed it all — freight shipments, passenger travel, and even two significant rail accidents that remain part of its story.

Now, the Old Freight Station depot has a new life as Riley’s Railhouse, where history, hospitality, and the love of trains come together.