Holiday rentals in Crook County

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).

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.

Gateway to Painted Hills! Downtown Prineville Loft

Completely renovated historic building in downtown Prineville. Walk to everything. Light filled, loft-style apartment featuring modern decor & furnishings. Great home base for your trip to Central Oregon. The Painted Hills are just less than an hour drive. Smith Rock is 25mins away. Designated bike storage available inside the loft. NOTE: The loft is on the 2nd floor of a walk-up building. There are approx. 25 steps leading up to the apartment and there is no elevator in the building.

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.

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.

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.

Panoramic Mountain View Oasis

Your high desert sanctuary awaits. Enjoy breathtaking panoramic mountain views from your second floor apartment, stargaze in the hot tub, cozy up outside by the wood-burning fireplace, and so much more! Only 2 miles from Brasada Ranch, convenient for weddings and events. Close to world-famous Smith Rock, centrally located between Bend, Redmond, and Prineville for a myriad of outdoor activities. Forget your worries in this serene and peaceful place!

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!

Grizzly Getaway

Relax with the whole family at this peaceful and unique private 1081 SF apartment that includes everything you need. At the elevation of 4300 ft, enjoy the view of the cascades from Mt. Jefferson to Mt. Batchelor. Excellent “home base” location for all Central Oregon activities. Apartment is connected to owners home with private entrance and no shared spaces. Access to the apartment is up 18 stairs.