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 Agness

4.97 out of 5 average rating, 141 reviews

Remote Riverfront Retreat 1 Bedroom Country Cabin

Escape to this beautiful and spacious cabin nestled aside the Mighty Rogue River. Let the sound of the river take you away from the hustle and bustle of city life. Located in the Wild & Scenic River Area of the Rogue River - Siskiyou National Forest, outdoor adventure awaits!! Cast your line for renowned Chinook Salmon Fishing or take a hike on many nearby trails. Pack a picnic and cool off in the beautiful clear blue water. Whatever your interest, you’ll find no shortage of outdoor activities.

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Guesthouse in Fort Klamath

4.81 out of 5 average rating, 359 reviews

Wood River Hideaway

Get away from it all in our cozy cabin on Wood River. Nothing fancy but everything you need. Great for couples, families, fishermen, photographers and anyone who loves a river and peace and quiet. No phone, no tv and no internet help you get away. Your cell may or may not get coverage here. (For urgencies, wifi/landline available in my main house). Watch the wildlife, kayak, splash in the river if you dare (it's cold!), play a game, read a book, enjoy the stunning beauty of this part of Oregon.

Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 398 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

Guest favorite

Guesthouse in Eagle Point

4.9 out of 5 average rating, 315 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, 223 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, 375 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 Port Orford

4.99 out of 5 average rating, 291 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 Central Point

4.94 out of 5 average rating, 807 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!

Guest favorite

Guesthouse in Roseburg

4.93 out of 5 average rating, 208 reviews

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.

Top guest favorite

Guesthouse in Grants Pass

4.97 out of 5 average rating, 203 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

4.95 out of 5 average rating, 171 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***

Top guest favorite

Guesthouse in Yachats

4.97 out of 5 average rating, 267 reviews

The Carriage House at Dragons Cove

Under a spell of centuries of wind and waves, Cape Perpetua awaits. Here you'll find The Carriage House, an enchanted cottage with views of tiny Dragons Cove, Laughing Gull Island, and the majestic Perpetua headland, highest point on the Oregon coast. It's hard to imagine a more pristine oceanfront setting. Two dozen harbor seals congregate and birth their young on the island.