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

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.

Yikes place

Relax with the whole family at this peaceful place to stay. Our little town offers lots of things to do In the summer Horse races, rodeos, fair, rock hounds, Pee wee rodeos I could go on. You will be close to Prineville reservoir, Ochoco reservoir, Ochoco mountains. Great for Hunters , fisherman , boaters. In town we have a theater, museum , antique stores, Restaurants, Community pool, Parks for the kids with a splash pad , golfers have 2 golf course.

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.

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.

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.

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!