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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.

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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! ❤️

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.

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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.

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.

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.

Brasada Ranch | High Desert Modern Luxury | Sauna

Relax with stunning mountain views from a spacious patio with a fire pit and seating, or unwind in a private sauna off the primary suite. Cook like a pro in a chef’s like kitchen with a professional stove, chef's grade ventilation, full cookware, dinnerware, a bar with complete glassware for wine, spirits, and cocktails, and a wine cooler. Fully equipped for travelers seeking comfort, convenience, and memorable moments.

Court St. Cottage | Downtown Prineville

Welcome to Court Street Cottage, a one-of-a-kind and cozy home nestled in the heart of Downtown Prineville, Oregon! Walk to shops, restaurants and coffee houses. Located just a stone's throw away from the historic Crook County Courthouse, this charming cottage is the perfect gateway to the breathtaking beauty of the Ochoco Mountains, Painted Hills and the Crooked River Backcountry. Managed by Desert Sage Rentals LLC

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!

Grand Escape

Stepping inside the Grand Escape! where you won’t forget your time in this romantic, memorable place. there is a place to sit outside and enjoy the sunset. Or even you would rather stay inside you can enjoy the reclining chairs and sir back and watch a movie on the firestick that is avb. for guest to use while their stay

Funky Bungalow in The Heart of Downtown Prineville

Warm. Cozy. A little funky. J Tree is a pet-friendly 2-bedroom, 1-bath stay right in the heart of downtown Prineville, Oregon. This older vintage-inspired bungalow has personality — colorful decor, unique art, a funky layout, and a comfortable feel that makes it an easy Central Oregon home base. Dream. Journey. Rest.