Guesthouse vacation 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

Sand Creek Cottage

Welcome to Sand Creek Cottage located in the heart of the beautiful Siskiyou Mountains near the Wild and Scenic Rogue River. Enjoy the warm, eclectic, feel of your own private Guest House. Sand Creek Cottage can be a destination retreat space or a base to explore the vast natural beauty, outdoor adventures, growing wine region and local tourism of Southern Oregon. We invite you to relax in the Outdoor Sauna, cozy up with a good book next to the wood stove and enjoy fruit from the Orchard.

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!

Oceanfront Luxury Guest House | King Bed Retreat

ALWAYS 5 STARS CLEAN, no pets, fresh. Come here, enjoy a luxurious, ultra private Guest House in garden. Safe, serene, green, gorgeous, meticulous grounds, private patio, big yard. NO CHORES FOR YOU! Contactless check-in. CalKing bed, luxury linens. Access to huge cliffside oceanfront deck & yard. Equipped gourmet kitchen. Personal gas BBQ, utensils, lawn & picnic area, safe, secure parking, estate lighting, washer, dryer, soap. Free fast dedicated WiFi. NOT SAFE FOR CHILDREN OPEN CLIFF.

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!

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

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.

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***