Ashland Cottages High St. & TCI

A beautiful, private retreat, in a great ‘walk to everything’ location. Our two bedroom cottages are incredibly clean, designed and handcrafted to enhance your stay and reflect the beauty of Ashland and the surrounding area. . .

Pioneer Street Vacation Homes

It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private, off street parking makes this home extra special in a charming downtown neighborhood.