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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.

Beach Bungalow in Prineville, OR

Bring the whole family to this great place with lots of room for fun. We welcome you to our stucco built Oasis in the high desert! Two roomy bedrooms with living room, full kitchen and laundry room, and bathroom with huge walk in shower. Private entrance and parking available. So much to do in the heart of central Oregon- stay for the rodeos, horse races, enjoy our quaint downtown, many outdoor activities, a short trip to the mountains and lakes. Come enjoy Prineville and stay with us! ❤️

Bitterroot Butte | Reservoir Views, Sleeps 10

Spacious group getaway sleeping 10 comfortably (up to 12 with couch and/or bringing an air bed). Stunning views of Prineville Reservoir and surrounding mountains. The reservoir is Oregon's first International Dark Sky Park — incredible stargazing from the property. Easy access to the lake for watersports, fishing, hiking, and biking, plus public lands for hiking and rockhounding right at the door. ⚠️ 4x4 or AWD required to access. No boat parking. Managed by Desert Sage Rentals LLC.

Lake front in Prineville~

Lake front privacy...Fish, Swim, water ski, kayak right here in your own back yard. Bring your horses to the Ochoco wilderness. Hike or rock climb at Smith Rock, take a day shopping in Bend or just have a relaxing time away enjoying Prineville! Please know the lake is a reservoir and depending on snowfall to completely fill the lake. Late summer the lake recedes because of the use of irrigation in the Prineville farm territory. Please use the boat ramp when the lake is low!

Romantic Ranch Oasis near Bend, Redmond,Prineville

This is a Must Stay Destination if you want to be close to everything Central Oregon has to offer yet in a quiet, relaxing ranch setting. Keystone Natural Cattle Ranch has Lots of room to spread out and enjoy country living while still being close to town! You will be very centrally located between Redmond, Prineville, Bend & Terrebonne. Only 8 miles to Downtown Redmond, 24 miles to Bend, Only 13 Miles to Prineville, 14 miles to Terrebonne and 7 miles to Brasada Ranch.

Visit Rip’s Cabin in the Heart of Prineville

Experience the best of Central Oregon in this stunning 2017 downtown Prineville home! Ideal for families and traveling working professionals, this charming residence offers a convenient location within walking distance of restaurants and shopping. After a day of work or exploration, relax and marvel at breathtaking sunsets and stargazing opportunities. With easy access to Bend, Smith Rock, and the Painted Hills, this is the perfect base for both adventure and productivity.

LaFollette by Stahancyk House

This Queen Anne cottage in Oregon's Ochoco Valley, built in the early 1900s, has a rich history in the sheep and wool industry. Built by Thomas H. Lafollette and Margaret J. Allen, the house was passed down through generations. After Hazel Sullivan's passing, the house fell into disrepair. A recent restoration has revitalized it, addressing foundation issues, lead paint remediation, and restoring original features. The updated living space blends the past with the present.

Charming Modernized 1938 Ranch Home

Enjoy a taste of ranch life in this modernized 1938 home. Located on a large, peaceful lot in downtown Prineville, guests can walk to many amenities. The picture windows offer views of colorful sunsets, deer and quail. Comfortably furnished and tastefully decorated, this home reminds guests of a cowboy lifestyle of yesteryear. Home features ceiling fans, portable fans, coffee maker, dishwasher, microwave, WiFi, smart TV, Blue Ray/DVD player, fans, and ample parking.

Cozy, stylish Bungalow in Downtown Prineville

Warm and Cozy bungalow in the heart of downtown Prineville, OR — the perfect Pet-friendly Central Oregon getaway. Walk to local shops, relax or work remotely in a warm, vintage-inspired space designed for comfort and ease. ✔ Comfortable beds with quality linens ✔ Natural light ✔ Fully stocked kitchen + Coffee Station ✔ Fast WiFi ✔ Smart TV ✔ Easy self check-in ✔ Free parking ✔ Washer & dryer ✔ Fenced backyard with doggie door Dream. Journey. Rest.

Ochoco Valley Cottage

A peaceful private guest cottage tucked into the foothills of the Ochoco Mountains. Enjoy wide open views, star-filled skies, and frequent wildlife right outside your door. Just 45 minutes from the Painted Hills and close to Walton Lake and Big Summit Prairie. Clean, cozy, and family-friendly with a unique loft sleeping area accessed by a ship ladder — perfect for couples, small families, and travelers wanting a quiet Central Oregon getaway.

The One Above the Rest w/Game Room

Discover the allure of Central Oregon in this captivating downtown Prineville home. Perfect for families and professionals, this charming house offers a prime location near restaurants and shops. Enjoy a game room with a pool table, darts, and arcade machines. Marvel at stunning sunsets and stargazing. Conveniently situated for exploring Bend, Smith Rock, and the Painted Hills. Your ultimate hub for adventure and relaxation.

High Desert Vista Home: Modern Trailside Retreat

Perched on Central Oregon's edge, this sleek 3 Bedroom home sleeps 6 (pet-friendly, 2 dogs <50lbs). Barnes Butte trails from backyard—hike, bike, views! Vaulted ceilings, big windows with vistas. Gas fireplace, modern kitchen with island. King primary with shower, 2 queens, 2 baths, laundry. Fenced yard, covered patio for sunsets & stars. Near downtown, Reservoir, Smith Rock, Bend, Ochoco. Adventure awaits!