Guest house holiday rentals in Southern Oregon

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

Free Bird Ranch-Oregon Adventures Home Base

Crater Lake National Park is NOT closed, only the 2 mile walking path that leads to a boat ramp is closed for renovation. The rim drive is open all year round. Find peace and serenity in the Rogue Valley. Enjoy stunning valley, Cascade views, and sunsets from the deck. Minutes from vineyards, a short drive to Table Rocks (10 min) & the Rogue River (2 min). On the way to Crater Lake (50 min) & near Ashland skiing (45 min). Unwind in comfort after your adventures. Long-term inquiries welcome!

The Sunset Ranch

Relax in the peace of a working mini-ranch where the sounds of chickens, crickets, frogs, and owls will quiet your mind. Sunset Ranch is just far enough away from the busyness of town to enjoy the most brilliant star-filled skies from the deck or take a short walk to the top of our property and watch the sun set over Klamath Lake! Situated off of Hwy 97, we are conveniently located just 5 minutes from Oregon Tech and Sky Lakes Medical Center. Downtown Klamath Falls is just 8 minutes away.

Serene Upstairs Studio with Bath & Kitchenette

This upstairs studio is surrounded by beautiful trees that gives you the impression of staying in a treehouse. Located in a panoramic rural area just 5 miles from downtown Grants Pass and 5 miles from downtown Rogue River. Perfect place to be away from the hectic city lifestyle, yet close enough to restaurants, local shops, wineries, jet boat rides, hiking trails and much more... In addition, this pictured-postcard location is 8 mins walking from Pierce Riffle County Park.

The Bliss/amazing rates/walk to DT/food/wine/shops

Welcome to the Bliss! Crisp, clean, & ready for your arrival! Thoughtfully curated with high-end linnens & amenities, ensuring you feel pampered from the moment you arrive. Tucked behind our main residence, this private sanctuary provides a peaceful escape while keeping you close (2 blks down)to the vibrant energy of local restaurants, wineries, boutique shops, & the lively Sat farmers market. 9am-1pm hotsprings, falls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

Most Spectacular Ocean Views - Studio East Upper

The Point provides the most amazing OMG view of the ocean and beach of the Oregon South Coast and possibly the world. You sit 100 feet above the water on our beach front property looking at the dolly dock pier and harbor to the east and Battle Rock and and a long stretch of beach to west. You can walk to the end of the property and enjoy your favorite beverage on the deck on the cliff above the water. You have truly magnificent views from our top-of-the-line studios.

Chalet in the Woods

Welcome to the little Chalet in the beautiful Oregon woods! Come relax and unplug in this charming private guest house situated on 4 acres, just 5 minutes from downtown Grants Pass and 3 minutes from grocery stores and shopping yet you feel as if you are out in the country far removed from anything and everything. This space was created to embody Swiss style living and the details speak to that. Comfortable and efficient.

Valhalla Cabin, King Bed, Hiking, close to Britt

Tranquility & hiking. 128 AC of wooded acreage to hike on. The flowers bloom in the spring! Come and see! We are located about 20 min from The Britt in Jacksonville. Check out their venue and list of performers! ***This is a NO SMOKING IN OR OUT of the unit/property, This cabin is NOT suitable for children, No animals allowed EXCEPT for service dogs. When there is snow, 4-wheel vehicles are advised***

The Friendly Den / Cozy, private couples retreat.

Welcome to the Friendly Den, a newly built, Scandinavian-inspired home nestled in Eugene’s official Friendly Neighborhood—a welcoming, working-class area just minutes from downtown. Our thoughtfully designed space is perfect for collegiate events, concerts, family visits, or simply unwinding in comfort and warmth.