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Artsy Guest House Nestled in the Rimrock

This property is truly an oasis from the hustle and bustle of city life. When you arrive, the massive rimrock wall will greet you; it is home to abundant wildlife (owls, deer, coyotes oh my). Shrouded by silence, the trill of frogs will put you to sleep. Mornings start with sunrise over the Ochoccos and full views of the valley and the crooked river at its base. Take a hike at Smith Rock, visit the Painted Hills or find yourself headed to town (Bend: 45 min, Prineville: 10 min, Redmond: 25 min).

The Nest at Brasada Ranch

Set on a spacious Brasada Ranch property, this modern detached casita is a calm and welcoming retreat with beautiful sunny exposure throughout the day. Thoughtfully designed interiors feel fresh and comfortable, with a cozy living area ideal for movie nights. Step outside to the patio to enjoy morning coffee, sunset views, Cascade Mountain vistas, or a soak in the private hot tub. An outdoor fire pit invites stargazing evenings, while upstairs kids have their own space to read, play, and unwind

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! ❤️

Tiny Pine house in the Ochocos at Wine Down Ranch

Cozy, country tiny home with deck, fire pit, views of meadows, and Ochoco National Forest. Interact with the horses, cattle, and dogs. Serene space with beautiful views of the Cascade mountains. Dark sky certified. View the Milky Way, many constellations, and a few galaxies. Located on 2100 acre Ranch, which is 11 miles from Prineville and 1 mile from the National Forest. Many outdoor activities are available - hiking, mountain biking, snowshoeing, birding, and much more.

The Pine~ Movie Theater & Apartment

One of the highlights of this Airbnb is its exclusive access to the attached historic movie theater located downtown Prineville. As a guest, you'll have the rare opportunity of having a private screening for you and your party outside of regularly scheduled movie times. Please see your host for those times to schedule your private viewing. The apartment features a fully equipped kitchen, 2 bedrooms, large great room, and plenty of sleeping space.

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.

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!

The Lookout at Brasada Ranch

Welcome to the Lookout! This expansive home boasts panoramic Cascade Mountain views, a sprawling lawn, patio & large built in gas fire pit. A covered terrace runs along the back where you can enjoy dinner, drinks and dramatic sunsets with friends & family. Inside find voluminous ceilings, a dramatic stone fireplace, open kitchen, large pantry & wine closet. Features 5 BR & a 2nd story bunk room.

Juniper Ridge Retreat

Peace, tranquility, and memory making await you at Juniper Ridge Retreat. This area has received the rare International Dark Sky Park designation bringing visitors from all of the world for premium stargazing. Amazing views of Prineville Reservoir and surrounding wilderness from all rooms and the wrap around deck allow you to take in the beauty of this unique area.

Brasada Ranch Cabin 89 | Hot Tub | Grill | Pool

Discover the perfect retreat at Cabin 89 in Brasada Ranch! This fully renovated cabin combines modern rustic charm with exceptional comfort, creating a true home-away-from-home experience. Enjoy breathtaking sunsets from the deck, featuring new outdoor furniture, and a dining area.

Stahancyk House

Stahancyk House is great for a larger group or family. Sleeps up to eight with a spacious living room, outdoor deck, and more. There are four bedrooms and five bathrooms. A large dining room. An EV charging station is our special bonus for EV drivers.