Family-friendly 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.

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

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.

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! ❤️

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.

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!

The Hideaway

Escape to The Hideaway, a cozy tiny cabin in the Ochoco Mountains of Central Oregon. Sleeps 2–4. Loft queen bed accessed by a steep ship-style ladder; limited headroom and may feel enclosed—those uncomfortable with small spaces or claustrophobia may prefer the futon in the main living area. Includes kitchenette, private bath with hot shower and composting toilet, Smart TV, and outdoor space. Unplug, relax, and enjoy nearby hiking and fishing.

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.

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

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.