Vacation 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.

Comfortable and quiet guest house

Come and enjoy the beauty of Central Oregon while you stay in this adorable, detached guest quarters in the hills of Powell Butte. This high desert property has views of some of the Cascades as well as Smith Rock. The guesthouse sits behind the main home on 5 acres for privacy. It is centrally located between Bend, Redmond and Prineville for a wide range of outdoor activities including easy access to Brasada Ranch and Smith Rock. Enjoy bird watching, wildlife, walks and incredible sunsets.

Lakefront House with Amazing View Near Bend Oregon

Located in Central Oregon, 50 minutes from Bend, this newly renovated 4600 sq-ft lakefront home is a rare piece of paradise! This property has over 200 feet of year round private lakefront shoreline onto a 1,100 acre lake. Stunning lakefront views from almost every room in the house, luxurious décor, 5 bedrooms, and incredible options for both indoor and outdoor entertainment. This home was specifically designed and built for the ultimate year-round get-a-way vacation or executive retreat!

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.

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.

COPPINI’S Creekside Camp, Painted Hills

Coppini Creekside Camp is “glamping” at its best. Our cabin sits away from it all at the bend of Thompson Creek. Nesteled amongst beautiful juniper trees. A fire pit ,outdoor cooking station and a cooler with ice waiting for your beverages and perishables.Inside is a comfy queen bed and loft with a single mattress. Cabin has bathroom with camp shower and toilet. Tent available for guests that want more of the camping experience. Come, relax and have a super experience.

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!

High Desert Retreat | Prineville

Welcome to the High Desert Retreat in Prineville! This charming 2-bedroom, 1-bath rental sleeps 4 and offers Wi-Fi, air conditioning, a kitchenette, and outdoor seating with a BBQ. Perfectly located near Prineville Reservoir, Ochoco National Forest, and Barnes Butte for hiking, fishing, and exploring. Ideal for families and outdoor enthusiasts seeking adventure in the High Desert! Professionally managed by Desert Sage Rentals LLC.

Brasada Ranch Luxury Cabin - 3 Beds - Views

Enjoy the beautiful scenery of the Cascade Mountains and Juniper trees from your own private balcony at Brasada Ranch! Plenty of space to entertain - large dining table + wrap-around deck with table fire pit outside. Fast internet, private work area, plenty of space for two families, and all the amenities. Just a quick walk to golfing, swimming, and much more that Brasada Ranch has to offer!

Creekside Cottage

Welcome to peaceful Creekside Cottage. One minute walk to beautiful downtown Prineville. Close to dining, groceries and gas. One step away from the bike path, and a stone's throw away from tranquil Ochoco Creek! Private, yet centrally located. Ample off street parking. Sleeps 6 adults, full kitchen, laundry. The home boasts beautiful artwork created by lovely local artist Kristine Cooper!