Guesthouse holiday rentals in Klamath River

Charming cottage, walk to town.

Our guests arrive at The Ashland Cottage and their first words are almost always the same: "It's gorgeous!" That's because the cottage delivers what Ashland visitors want- comfort, charm and a walkable location just 10 minutes from downtown and OSF theaters. Though newly built, the cottage echoes the Craftsman character of our 1920s main residence. As a fully separate house with its own private entrance, it offers spacious living with high ceilings, abundant natural light and inspiring views.

Location · Value · Amenities

Historic carriage house close to downtown Ashland

Explore downtown Ashland in a private carriage house! This home was built in 1884 and is on the property of an historic Victorian. Full kitchen with stove, dishwasher and refrigerator. Pellet stove in the living room as well as wall vented heating. Enclosed yard. Separate bedroom and en suite with a tub/shower combo and washer and dryer. Off street parking. HBO and Netflix included. 10 minute walk to downtown Please note the only bathroom is through the bedroom. Dog friendly - no cats please

Value · Family · Parks

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

Location · Family · Parking

Whispering Trees Cozy Country Cottage

The "Whispering Trees Luxury Cottage" is your quiet, cozy country getaway just 2 miles from town, across the street from the Mad River and 5 miles from the beach. Cruising up the long driveway, you'll be welcomed by our mustang, and adorable donkeys. We welcome guests of all backgrounds and love making new friends. Having lived on the North Coast for over 40 years, we're a great resource to make your stay memorable. We have another popular suite on the property: Airbnb.com/h/countryblueroom

Value · Family · Sleep quality

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.

Location · Value · Checkout

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!

Value · Family · Skiing

C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

Location · Value · Comfort

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. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

Family · Value · Nearby

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Value · Location · Access

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!

Value · Family · Bathroom

Newer Cozy Guest Cottage w/ Saltwater Spa!

Find style and comfort in this new construction cottage. Queen bed is a comfortable Sealy. Pullout sofa is a Queen La-Z-Boy Tempur-Pedic. Recliner in living area. Cotton sheets with 680 thread count. Twin air mattress available. Fiber internet w/ ultra fast Wi-Fi. Smart TV with Netflix and apps. Black out blinds in bedroom. All blinds top down or bottom up to let light in and have privacy. On demand hot water heater. USB ports on nightstands, lamps and in kitchen.

Family · Value · Decor

Tranquil Studio Near Scenic Redwood Hwy

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 (dry in summer). Guests who book one night often wish they had stayed longer.

Family · Value · Bathroom