Guesthouse vacation rentals in Southern Oregon

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Top-rated guesthouse rentals in Southern Oregon

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 819 reviews

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! HOTTUB CLOSED until mid-September 2025.

Top guest favorite

Guesthouse in Medford

4.93 out of 5 average rating, 410 reviews

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

Top guest favorite

Guesthouse in Grants Pass

4.98 out of 5 average rating, 250 reviews

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.

Guest favorite

Guesthouse in Eagle Point

4.91 out of 5 average rating, 324 reviews

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!

Top guest favorite

Guesthouse in Klamath Falls

4.98 out of 5 average rating, 241 reviews

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.

Top guest favorite

Guesthouse in Brookings

4.98 out of 5 average rating, 387 reviews

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.

Top guest favorite

Guesthouse in Brookings

4.97 out of 5 average rating, 191 reviews

Oasis by the Waves: Serene Oceanfront Cottage!

Oceanfront Paradise, private 480sqft kitchenette cottage nestled within serene oceanfront gardens, year round to enjoy. Perched on a cliff with stunning views of Sporthaven Beach along the breathtaking Southern Oregon Coast. This cozy retreat offers ultimate privacy for couples or solo adventurers, queen-sized bed, a comfortable living and dining area, and outdoor patio. Enjoy tranquility and cleanliness in this private oasis situated on a peaceful street. Only 1/2 mile stroll to the ocean

Top guest favorite

Guesthouse in Grants Pass

4.99 out of 5 average rating, 163 reviews

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!

Guest favorite

Guesthouse in Jacksonville

4.93 out of 5 average rating, 1,088 reviews

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.

Top guest favorite

Guesthouse in Port Orford

4.99 out of 5 average rating, 309 reviews

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.

Top guest favorite

Guesthouse in Grants Pass

4.97 out of 5 average rating, 210 reviews

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.

Guest favorite

Guesthouse in Jacksonville

4.96 out of 5 average rating, 180 reviews

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***