Follow the Applegate Wine Trail.
Explore tasting rooms, routes, and wine events through the official trail guide.
Explore the wine trail ↗555-555-5555
mymail@mailservice.com
ROOTED HERE. READY TO WELCOME YOU.
Unhurried mornings. A place to gather.
A beautiful home for everything in between.
YOUR GETAWAY STARTS HERE
MAKE YOURSELF AT HOME
From a quiet cottage for two to a retreat for the whole family, find your own corner of Southern Oregon.
Dates, availability, and final pricing are confirmed on our secure Hostfully booking site.
Check dates & availability ↗THE SISKIYOU STAYS DIFFERENCE
A Southern Oregon team who knows the area and is here to help with your stay.
Professionally managed and cleaned homes, with space to settle in.
Check availability, see pricing, and reserve your home through our booking site.
THE SOUTHERN OREGON FIELD GUIDE
Wine-country afternoons, outdoor adventures, and something happening just around the corner.
Plan your tasting route with Travel Medford’s Rogue Valley wine map.
Open the full wine map ↗
Interactive wine guide ↗
Map provided by Travel Medford. Confirm tasting-room hours and reservations, and plan a designated driver.
Explore tasting rooms, routes, and wine events through the official trail guide.
Explore the wine trail ↗Pair a Jacksonville stay with a performance. Check the official schedule for dates and tickets.
Browse Britt’s calendar ↗Check road access, weather, and park conditions before setting out.
Plan your park visit ↗Browse the local food guide or ask our team for suggestions near your home.
Explore local food ↗Selected upcoming events. Confirm dates and tickets with the organizer.
Listings checked October 26, 2026. Past events hide automatically; additions require site updates.
Full regional events calendar ↗FAMILY RUN. ROOTED IN SOUTHERN OREGON.
Thoughtful stays, room to reconnect, and a place you’ll want to return to.
We’re Shon and Chelsea, the family behind Siskiyou Stays. Our small business began with one short-term rental and a simple belief: where you stay can become one of the best parts of your trip.
After years of traveling as a young family, we came to love the feeling of a home away from home. We valued having space for everyone to sleep comfortably, a kitchen where we could make a big family breakfast, and a place to relax together without feeling crowded into a hotel room. Those everyday moments shaped the kind of hospitality we wanted to share.
As we gained experience hosting our own rental and built strong connections in our community, we began offering our management services to other homeowners. Siskiyou Stays grew from that first home into a collection of Southern Oregon stays, with the same personal care at its heart.
Today, our homes welcome many kinds of travelers and budgets—from a convenient city stay or a home near historic downtown to a spacious family getaway or a quiet cabin in the woods. We bring thoughtful comforts and a sense of luxury to a range of settings and price points.
Southern Oregon is our home, and we hope you’ll fall in love with it as much as we have. Above all, we want you to feel comfortable, make lasting memories, and leave looking forward to your next visit.
Find your home away from home ↗GOOD MEMORIES, IN THEIR WORDS
Selected positive guest review excerpts, with attribution and source links.
A CHANGE OF SCENERY IS CALLING