2nd Street Cottages

2nd Street Cottages is located on a quiet side street in the historic and lovely Railroad District. This is the perfect location providing all of the comforts and charm of a historic (renovated) home and the option of not having to drive to experience all that downtown Ashland has to offer. Just two short blocks to theatres, unique shops, world class dining, art galleries, tasting rooms, day spas, entertainment and people watching.

Abbott's Cottages

Nestled around a central courtyard, Abbott's Cottages offer delightful accomodations ranging from a charming one room studio to a spacious three bedroom house. . .

Ashland Commons - Groups, Families, Hostel

Perfect for individuals, families, small or large groups. Three units w/kitchen, common area, A/C, WiFi, parking, laundry, and patios. Private, family rooms, and dorms. Mtn. views; walk to downtown/OSF. A relaxing, affordable option.

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's Main Street Inn

The new owner of Ashland's Main Street Inn intends to continue to offer top-quality travelers accommodations. Two spacious suites with full kitchens provide luxury and comfort in the elegant 1883 Victorian located two blocks from the Plaza.

DeLaunay House

DeLaunay House - Location Location! Just a block from town and Shakespeare. Enjoy this historic craftsman style bungalow with fully equipped cooking facilities, mountain views, and lovely front porch. Families welcome! Sleeps up to 15

Jacksonville Inn

The Jacksonville Inn is a historic bed and breakfast inn, restaurant, and wine shop located in the heart of the National Historic Landmark town of Jacksonville, Oregon.

Oak Street Cottages

Just a block to downtown, Oak Street Cottages are Ashland's very first vacation rental, now 20 years being "Ashland's Favorite Family Inn" Rent one cottage or all four!

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.

RedTail Inn

Celebrate the grand opening of Ashland's First Eco-boutique Inn! This historic home, built by one of Ashland's founders, is located one block off of the business district and four blocks from Shakespeare.

The Ashland Hostel

The Ashland Hostel provides clean, friendly and economical accommodations in an historic home just two blocks from restaurants, shops and the Oregon’s famous Shakespeare Festival theatres.

Weisinger Family Winery

Weisinger's of Ashland is a family owned and operated winery situated on a hill overlooking the Rogue Valley. Founder, John Weisinger, was a pioneer in developing the Rogue Valley as awine producing region. His son, our Winemaker, Eric Weisinger, joins him today. Together their emphasis is on quality and capturing the finest character from the fruit grown in the Rogue Valley Appellation of Southern Oregon.

Willow Witt Ranch

Nestled nearly a mile high in the Cascades just east of Ashland, 440 acre Willow-Witt Ranch is the hidden jewel of Southern Oregon.