Holiday rentals in Jefferson County

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Near SmithRock pets ok private heated bungalow

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Cabin in the Ochocos

Our cabin/guest house is located on 32 acre forested property next to the main house and is a perfect base camp for hikers, bikers, hunters, dark sky and winter sport enthusiasts. It overlooks Upper McKay Valley, is one mile from the north entrance of Ochoco National Forest and 10 minutes north of downtown Prineville. Ideal for 2 but can accommodate 4 people to share the amenities of a small scale fully equipped home. Amazing views with farm animals to round out the country living experience.

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

With 2100 acres nestled against the Ochoco NF, our ranch is a family-owned working ranch. Dark sky certified. Amazing view of the Milky Way and stars. Scenic meadows, managed forest lands, and rock vistas make up the landscape. Enjoy the slow-paced country lifestyle in an authentic ranch setting with horses, cows and dogs. Guests are welcomed and encouraged to enjoy the whole property. Many hiking areas and views to explore. Usual snowy winters make great fun for cc skiing and snow shoeing.

Camp Sherman Oregon Private Cabin Mt Jefferson

Small Cabin located near Lake Creek Lodge and Fire Station/Community Hall on the main road into Camp Sherman. This cabin is located on 1 acre property with grass and park area that includes, campfire area, horseshoe pit and pond (no swimming). Bike & hike trail adjacent to the store /river Perfect getaway, great condition with granite island and counter tops, knotty alder cabinets. Over 300 DVD collection. Wi-Fi Starlink, if remote working is necessary. GUESTS MUST CLEAN THE CABIN!!!

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

Steelhead Falls Log Cabin

Enjoy a restful time in our waterfront log cabin along the Deschutes River. Location is perfect for watching wildlife, fly fishing, quiet relaxation, and has easy access to hiking and rock climbing at Smith Rock and Lake Billy Chinook. Steelhead Falls is a a short hike away. Bend and Sisters are near. Unfortunately, we cannot accommodate even small weddings. We recommend access to AWD vehicle with either chains or snow tires in winter. Dog friendly- sorry, no cats.

Classic Cozy Cabin with Awe-inspiring Views

Come enjoy rustic relaxation in our Classic Cozy Cabin. It's 208sq ft of cozy comfort in the breathtaking Crooked River Gorge. The private cabin is equipped with a private bathroom, kitchenette, wifi, cable TV, private deck, and just enough leg room to rest, relax and unwind after a day of adventure in beautiful Central Oregon! And the cabin is pet friendly! (Pet fee required, max 2 pets). It's a great place to kick off your boots and stay awhile!

Experience Serenity w/ Mountain Views & Home Gym

Escape to a serene and stunning mountain view retreat in the high desert. This ranch home offers an unparalleled connection with nature, set on a beautiful farm and surrounded by breathtaking views of the Cascade Mountains. Perfectly located just 5 minutes from downtown Madras, and within easy reach of other exciting central Oregon towns, this retreat offers the perfect blend of peaceful seclusion and convenient access to local attractions.