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 Haus

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom.

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.

Chateau Herbe II

Chateau Herbe II: A French castle estate that combines elegance with enchantment. Nestled on 27+ acres, it offers stunning mountain views, a rose garden, water features, and luxurious accommodations. Perfect for weddings, events, and exclusive stays.

Good Life Property Group

At Good Life Property Group, we take a proactive approach to vacation rental and property management, ensuring ‘no bad stays’ for all guests. We believe in staying ahead of any potential issues and keeping our clients informed every step of the way. Our approach has helped us to build long-term relationships based on trust and transparency, catering to both property owners and vacationers locally and globally.

Green Springs Inn

Green Springs Inn & Cabins offers a sustainable getaway opportunity in a forested setting near the crest of the Southern Cascades. For a generation, Southern Oregonians and visitors from afar have made Green Springs Inn a breakfast, lunch and dinner destination.

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.

McCracken Property Management

We're a boutique property management company specializing in short term rentals (Airbnbs) in Ashland! With a blend of experience as owners/investors as well as property managers we know what it takes to take care of your baby (property) and make sure our guests do too!

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!

Swank House

CLASSY VIBES, LOCAL TOUCHES At every Swank House, your comfort is covered. Live it up with delightful touches around every corner — intentional, thoughtful, and locally-rooted in Ashland. 9 locations. Steps to Shakespeare theatre. Your Swank House awaits.

The Peerless Hotel

Welcome to the historic Peerless Hotel, where comfort and quietude combine in this rare and exceptional historic property. This boutique hotel, which is listed on the National Register of Historic Places, is beautifully situated in an exceptionally quiet neighborhood that is walking distance to the Oregon Shakespeare Festival, Lithia Park, and the shopping and dining destinations of the Ashland Plaza.

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.