1900 The Guest Houses

The Historic ‘1900’ House and Guest House is the best of downtown Ashland. The house and guest house are located less than five blocks to the renowned Oregon Shakespearean Festival, Lithia Park, art galleries, retail stores and restaurants.

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. . .

Ashland Haus Retreat

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom one bath 1900s home has many new renovations (floors, appliances, furniture--). . .

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.