Guesthouse vacation rentals in Southern Oregon

Find and book unique guesthouse rentals on Airbnb

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 Cottage Grove

4.93 out of 5 average rating, 177 reviews

Swinging Bridge private and bright guest cottage

*** Please read entire listing before booking: Quaint cottage set behind Craftsman home built in 1926. Private entrance w/keyless entry. Bathroom is private and dedicated to guests but is *connected to the main house* and only steps away from cottage. Bathrobes and slippers provided for guest use. Access to yard with fire pit and BBQ. Room has mini fridge, microwave, and toaster oven as well as amenities for coffee and tea. Guest WIFI is high speed. Roku TV for streaming. Free street parking.

May 16 – 23

G$18,137 GYD per night

Guest favorite

Guesthouse in Roseburg

4.99 out of 5 average rating, 206 reviews

Blissful/Big picture windows/sun loungers/AC

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.

Oct 7 – 14

G$19,106 GYD per night

Guest favorite

Guesthouse in Brookings

4.98 out of 5 average rating, 314 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.

Oct 20 – 27

G$33,213 GYD 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

G$26,055 GYD per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 512 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.

Dec 16 – 23

G$28,591 GYD per night

Guest favorite

Guesthouse in Gold Hill

4.92 out of 5 average rating, 166 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

Oct 14 – 21

G$30,176 GYD 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.

Feb 26 – Mar 5

G$73,111 GYD per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 183 reviews

Wood Hamlet - Picasso Cottage by Downtown, kitchen

Our 'Picasso Cottage' sleeps up to 2 adults and is perfect for those who wish to enjoy artful living close to downtown Ashland! The space is the entire bottom floor of Carriage House, with full bathroom, bedroom (queen bed) with sitting area, washer/dryer, living room and full kitchen. Between shows relax on patio or by the swimming pond in garden. Private parking behind Carriage House. Walk to theater! (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Aug 8 – 15

G$25,407 GYD per night

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 709 reviews

BEE WELL Organic Spa Garden Studio

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!

Jul 22 – 29

G$23,169 GYD 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 9 – 16

G$23,977 GYD 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***

Dec 10 – 17

G$21,951 GYD per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 155 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.

Jan 26 – Feb 2

G$22,120 GYD per night