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! ❤️

Noble by Stahancyk House

This unique property offers a nostalgic journey back to the 1930s, blending vintage charm with modern amenities. We have three bedrooms. The master suite features a king-size bed with high-end bedding, and an en-suite bathroom. A second bedroom with a queen-size bed, high-end bedding. A kids bedroom with twin beds that embody a 1930s cowboy and cowgirl theme. There are numerous vintage touches and art throughout to complete the vintage theme. High end bedding and linens are included.

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.

Lakefront Retreat | Lake Ochoco

Welcome to Lakefront Retreat on Ochoco Lake. This peaceful 4BR/2BA home sleeps 10 with direct lake access for kayaking, fishing, and swimming. Relax on the deck with sunset views in a fenced yard that is dog friendly. Spot deer, antelope, and hawks, and enjoy stargazing under clear Central Oregon skies. Includes A/C, Wi-Fi, smart TV, and full kitchen. Quick access to the Ochoco Mountains and Painted Hills. Professionally managed by Desert Sage Rentals LLC.

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!

Lake front home on the Prineville reservoir

Nice updated home a 3 min walk to the lake. Enjoy your time in our cozy 1200 sq ft 3 bedroom 2 bath home over looking the Prineville Reservoir. The home is fully furnished with a well stocked kitchen. Our home and area is perfect for outdoor activities, guests do some of the following: Hiking, biking, swimming, fishing and trails. Just minutes away from 2 state parks, 2 boat ramps and easy shore launch. Recently added 2 kayaks with vests.

Brasada Ranch Cabin 78| Mtn & Golf Views| Hot Tub

Escape to your own private mountain getaway in this stunning, secluded cabin designed for comfort, relaxation, and connection with nature. Featuring two full suites, this home is perfect for couples, families, or friends looking for both privacy and togetherness. Enjoy the brand-new hot tub on the spacious back deck under the stars, unwind by the cozy fireplace, and stay connected with fast Starlink internet throughout your mountain retreat.

Juniper Cabin: 3BD Cabin at Brasada Ranch Resort

Relax and recharge at Juniper Cabin, a luxury 3-bedroom retreat in Brasada Ranch Resort. Enjoy a cozy living room with a stone fireplace, a fully stocked gourmet kitchen, and private en-suite baths in every bedroom. The spacious deck overlooks the 8th hole, complete with a fire pit, outdoor TV, BBQ, and hot tub. Guests also have access to resort pools, spa, golf, dining, and more — the perfect Central Oregon getaway!