Guesthouse vacation rentals in Southern Oregon

4.98 out of 5 average rating, 803 reviews

Douglas Fir Cottage - peaceful getaway near U of 0

Architecturally designed backyard cottage located one mile south of the University of Oregon adjacent to Eugene's historic Masonic Cemetery. This contemporary Northwest space includes a spacious living area with a new king-sized bed, smart TV, WiFi, kitchen, bathroom, private sauna and hot tub, and a spacious deck to enjoy beautiful sunsets. Located within walking distance to the University, coffee shops, Amazon Pool, and neighborhood stores. Enjoy dedicated parking and a beautiful setting.

4.98 out of 5 average rating, 132 reviews

Hillside Cabin Retreat

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.

4.93 out of 5 average rating, 435 reviews

Guesthouse in Medford

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

Guesthouse in Klamath Falls

A scenic view of a sunset casts a warm glow over expansive green fields and distant hills. The peaceful landscape is complemented by a clear sky filled with soft clouds, while the sun's rays illuminate the tranquil waters of Klamath Lake in the background.

4.98 out of 5 average rating, 279 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.

Guesthouse in Klamath Falls

4.99 out of 5 average rating, 134 reviews

The Cozy Timber Loft

This unique place has a style all of its own. It offers peaceful tranquility and a place to unwind. It also offers a king size bed and a quiet work space. It is in walking distance to Klamath Community College and off Hwy39 for quick access to lava beds and the California boarder. Minutes from the Airbase, Hospital and Downtown. For those longer stays it has a washer/dryer. Come enjoy a small piece of country living that takes you to a relaxing hideaway. It is definitely home away from home

Guest favorite

4.92 out of 5 average rating, 180 reviews

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!

A modern kitchen is visible, featuring stainless steel appliances, including a refrigerator and oven. Ample counter space with a light-colored surface complements dark cabinetry. Skylights allow natural light to illuminate the area, enhancing the airy feel. A sink and dishwasher are also included.

4.98 out of 5 average rating, 453 reviews

New Studio 1,100 sq. ft. Guest House with views

We are located in the South Hills of Eugene. Close to U of O with easy driving access to amenities. The garage guest house sits on 3 wooded acres w/ south views to Creswell and winter views of the Three Sisters to the east. Built in 2020, the studio features a large walk-in shower, full kitchen, and laundry amenities. Sleeps 6 (King, double sleeper sofa, and two twins) Parking for multiple cars if needed. Unwind in a peaceful, natural Oregon setting, we look forward to hosting you.

The entrance to the cottage is framed by a rustic trellis and surrounded by lush greenery. A wooden deck leads up to a white door, providing a welcoming access point. Sunshine filters through the leaves, adding a natural brightness to the scene.

5 out of 5 average rating, 246 reviews

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

The exterior of a guest house is shown, featuring a light yellow facade and large windows. A deck with white chairs and a table is visible, surrounded by green grass and landscaping stones. A flowering tree provides shade, complementing the serene outdoor space.

4.89 out of 5 average rating, 140 reviews

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

A spacious living room is presented with stylish furnishings, including a gray sofa and a patterned area rug. Natural light filters through the large windows. A spiral staircase leads to the loft above, while double doors open to the outdoor space.

4.99 out of 5 average rating, 648 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 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.

The exterior entrance showcases a charming stone structure with large windows. Lush greenery and colorful flowers, including azaleas, fill the landscaped garden. A covered breezeway leads to the main entrance, inviting guests into a tranquil outdoor space surrounded by nature.

4.97 out of 5 average rating, 319 reviews

Sunny Studio in the Friendly

Cozy up in this sunny studio located in the Friendly neighborhood. Snuggle up in the comfy queen bed by the gas fireplace. A wine fridge chills your food and beverages. A private full bathroom—separate from the studio—is accessible by a 40-foot lighted and partially covered walk to the garage. Enjoy the quiet back yard, patio, and garden. Restaurants, shopping, and parks are within a short walk. We welcome up to two well-behaved guest dogs with responsible owners.