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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Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 583 reviews

Orchard Home Cottage * ~ Private, Cozy, Peaceful *

*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

Jul 19 – 26

ﺩ.ﺇ323 per night

Guest favorite

Guesthouse in Roseburg

4.99 out of 5 average rating, 205 reviews

Blissful Guesthouse Outdoor living rm/sun loungers

Welcome to the Bliss, your serene escape awaits! Picture yourself unwinding in our courtyard, on one of our sun loungers sheltered by a 15-foot umbrella. As the day turns to evening, indulge yourselves into the outdoor living room with ambient lighting, firepit, TV, curtains Those seeking a bit of playful diversion, will enjoy our Arcade/playoom Meanwhile, our variety of outdoor games, & picnic area. We are offering you a rejuvenating retreat that's both soothing and exhilarating.

Dec 5 – 12

ﺩ.ﺇ342 per night

Guest favorite

Guesthouse in Brookings

4.98 out of 5 average rating, 312 reviews

Luxe Private Oceanfront Guest House with King bed

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.

Dec 22 – 29

ﺩ.ﺇ596 per night

Guest favorite

Guesthouse in Eagle Point

4.91 out of 5 average rating, 252 reviews

Free Bird Ranch-Oregon Summer Adventures Home Base

You’ll love the peace and serenity this private guest house brings! We are minutes away from beautiful vineyards. On the path- (50 minutes) to CRATER LAKE where you can sightsee, hike, and snow shoe. Go fishing on the Rogue 5 minutes away! Enjoy the deck that overlooks the views of the valley and view’s of the CASCADES AND TABLE ROCK which is a 5 minute drive to the entrance. Ashland ski resort is 45 minutes away. Come back to a relaxing and cozy home after your adventures in the Rogue!

May 8 – 15

ﺩ.ﺇ468 per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 510 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Jan 2 – 9

ﺩ.ﺇ513 per night

Guest favorite

Guesthouse in Gold Hill

4.92 out of 5 average rating, 165 reviews

Octagon Studio / Beautiful Rogue River property

Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy

Nov 13 – 20

ﺩ.ﺇ542 per night

Guest favorite

Guesthouse in Port Orford

4.93 out of 5 average rating, 223 reviews

Most Spectacular Ocean Views - Studio

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

Mar 29 – Apr 5

ﺩ.ﺇ1,311 per night

Guest favorite

Guesthouse in Roseburg

4.94 out of 5 average rating, 172 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.

Sep 4 – 11

ﺩ.ﺇ430 per night

Guest favorite

Guesthouse in Grants Pass

4.95 out of 5 average rating, 144 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 2 miles 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.

Jan 20 – 27

ﺩ.ﺇ602 per night

Guest favorite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 134 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***

Aug 11 – 18

ﺩ.ﺇ406 per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 154 reviews

Starthistle Cottage in Applegate wine country

Rural cottage in the beautiful Applegate Valley. Peaceful with beautiful views of the landscape and wildlife. Closest lodging to Woodrat Mountain launch for paragliders & hang gliders. Nestled in the heart of the Applegate Wine Trail and the Southern Oregon Lavender Trail. Close to historical Jacksonville for the Britt Festival. Easy access to Applegate Lake and surrounding hiking trails.

Nov 17 – 24

ﺩ.ﺇ395 per night

Superhost

Guesthouse in Langlois

4.9 out of 5 average rating, 172 reviews

Pacific View Country Cottage

Located just 7 minutes from the beach, this studio lies on a hill with ocean views. It has 1 Queen bed and 1 bath with a clawfoot soaking tub. It is nestled in an orchard of fruit trees, blackberry bushes, and flower gardens. If you enjoy walking, there is a path that will lead you through 10 acres of forest, full of huckleberry bushes, ferns, large trees, and lovely streams.

Jan 9 – 16

ﺩ.ﺇ501 per night