Guesthouse holiday rentals in Southern Oregon

Hillside Cabin Retreat- 3.5 miles to Hayward Field

Escape to our tranquil guesthouse nestled in the woods, offering a private retreat just minutes from Eugene's city center & the University of Oregon. This cozy cabin features a well-equipped kitchenette, luxurious outdoor shower & spacious deck perfect for enjoying meals while observing local wildlife & sunsets. Unwind in the hammock & fall asleep to the sounds of nature. Conveniently located near Hayward Field & downtown Eugene, our guesthouse provides a unique blend of serenity & convenience.

Value · Location · Indoor spaces

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

Value · Family · Solo travel

Tranquil Studio Near Scenic Redwood Highway

Tucked amongst the trees, 8 miles west of Grants Pass, this charming studio feels like stepping into a quiet fairytale—birdsong and fresh air welcome you in. Enter through the cottage garden into a warm, thoughtfully designed retreat that balances convenience with nature. Perfect for road trippers or exploring the Redwoods, the studio features a spacious deck overlooking a seasonal pond with a stone bridge straight out of a fairytale. Guests who book one night often wish they had stayed longer.

Location · Family · Indoor spaces

Wood River Hideaway

*New reduced price...lots of winter damage in the yard* 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. 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.

Location · Family · Cleanliness

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.

Family · Location · Outdoor spaces

The Loft@Paradise Point. Hot tub w/stunning views!

Relax and unwind at this unique, secluded, sparkling clean, getaway. The Loft is situated behind a private security gate on top of a mountain. It has breathtaking views yet is only 10 min. from town and in the heart of some of the greatest wineries in Oregon. The bedroom has a romantic fireplace and access to a private deck. Equipped with a Refrigerator, K-Cup Coffee Maker, Air-Fryer, Toaster Oven & Microwave. Soak in the new luxurious hot tub that has WIFI. Fire pit offered when permitted.

Location · Check-in · Decor

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

Family · Location · Decor

La Petite Maison + Hot Tub

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

Family · Location · Amenities

Sun studio guesthouse with private entrance

Ask about an early check-in and 5 minute drive to the airport! Kick back and relax in this calm, sun soaked studio guest house. This space is perfect for someone in need of a getaway from everyday life. Wake up with the sun, make some coffee, work from home with peace and quiet. Also great for a romantic getaway with your sweetie. Queen bed some mood lighting. Watch some tv on our roku and stair at the stars through the skylights. Enjoy a private entrance with outdoor seating.

Location · Family · Air conditioning

Most Spectacular Ocean Views - Studio East Lower

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.

Value · Location · Accuracy

Rogue River Retreat with Views You’ll Never Forget

Immerse yourself in the stunning beauty of the Rogue River at this serene retreat. Wake up to breathtaking sunrises and unwind with tranquil sunsets, all framed by expansive river views from the cozy living room, bedroom, or spacious covered patio. Why You’ll Love It: Epic Wildlife Views: Spot ducks, geese, beavers, osprey, and even majestic eagles in their natural habitat. Prime Riverfront Vibe: Savor every moment with panoramic river vistas from indoors or out.

Family · Location · Checkout

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***

Location · Value · Indoor spaces