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Vacation Properties


The Pioneer - Craftsman House>

Downtown Ashland - Closest to OSF!

It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and 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.

The Space

This two-story, modern home has three bedrooms. The master bedroom has a king-sized bed and the guest rooms each have queen-sized beds. A spacious living room includes a comfortable sofa bed that sleeps two, making this home the perfect location for up to 8 guests. Enjoy cooking in the modern, fully appointed kitchen and relax with a glass of wine on either the upper balcony or lower patio. The home has two full bathrooms with shower stall downstairs and jetted tub upstairs.

Interaction with Guests

You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!

Prices start at $325


Rear House

  • Private Parking
  • Full Kitchen
  • Jetted Tub
  • Wireless Internet
  • Flat Screen Television
  • Cable TV
  • Fireplace
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Outdoor Seating