Follow the Applegate Wine Trail.
Explore tasting rooms, routes, and wine events through the official trail guide.
Explore the wine trail ↗SOUTHERN OREGON, PERSONALLY HOSTED.
ROOTED HERE. READY TO WELCOME YOU.
Find your
Southern Oregon.
Unhurried mornings. A place to gather.
A beautiful home for everything in between.
YOUR GETAWAY STARTS HERE
A place that feels like you.
MAKE YOURSELF AT HOME
Distinctive homes.
Memorable stays.
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 local welcome.
A thoughtful stay.
Real people, right here.
A Southern Oregon team who knows the area and is here to help with your stay.
A home, cared for.
Professionally managed and cleaned homes, with space to settle in.
Book with us directly.
Check availability, see pricing, and reserve your home through our booking site.
THE SOUTHERN OREGON FIELD GUIDE
A local way
to spend the day.
Wine-country afternoons, outdoor adventures, and something happening just around the corner.
Explore wine country.
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.
Make a night of Britt.
Pair a Jacksonville stay with a performance. Check the official schedule for dates and tickets.
Browse Britt’s calendar ↗Spend a day at Crater Lake.
Check road access, weather, and park conditions before setting out.
Plan your park visit ↗Find your next favorite table.
Browse the local food guide or ask our team for suggestions near your home.
Explore local food ↗What’s happening nearby.
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 ↗A FAMILY WELCOME
A home away
from home.
We’re Shon and Chelsea, the family behind Siskiyou Stays. What began with one vacation rental grew from our love of family travel, comfortable homes, and Southern Oregon.
We’re here to help you settle in, reconnect, and discover a place you’ll want to visit again.
Meet the family behind your stay ↗GOOD MEMORIES, IN THEIR WORDS
The stays that
stay with you.
Selected positive guest review excerpts, with attribution and source links.
A CHANGE OF SCENERY IS CALLING
Your next good memory
starts with a stay.
Find your Southern Oregon ↗
