Guesthouse 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.

New 1 room 1,100 sq. ft. Guest House with views

We are located in the South Hills of Eugene. Close to U of O with easy driving access to amenities. The garage guest house sits on 3 wooded acres w/ south views to Creswell and winter views of the Three Sisters to the east. Built in 2020, the studio features a large walk-in shower, full kitchen, and laundry amenities. Sleeps 6 (King, double sleeper sofa, and two twins) Parking for multiple cars if needed. Unwind in a peaceful, natural Oregon setting, we look forward to hosting you.

Tranquil Studio Near Scenic Redwood Highway

The studio offers a perfect balance of proximity to town and the tranquility of nature just 8 miles west of downtown Grants Pass. Enter the unit through a flourishing garden and enjoy a cozy, clean oasis. This is a great stopover for road trippers and a convenient home base for exploring the Redwoods and Rogue River. The unit features a spacious deck overlooking a seasonal pond (dry in summer). If you're seeking peace, quiet, and a restful night's sleep, this is the place for you!

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)

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

Riverfront Flower Farm Retreat

Welcome to Rustic River Farms! Situated on 5.5 acres in wine country along the Umpqua River, our riverfront guest house offers a quaint, quarky space to unwind. During summer months you can take in the views of lavender and seasonal flowers in our field. We are also in the heart of some awesome fish runs. A perfect base camp for the fisherman or couples looking for a quiet retreat, which can also accommodate 1 adult or 2 children on the sleeper sofa.

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.