Holiday rentals with outdoor seating 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.

Luxury Bungalow w Hot Tub at Brasada Ranch (21+)

THIS IS A RESORT-MANAGED LISTING, GIVING YOU ACCESS TO ALL BRASADA RANCH'S LUXURY AMENITIES Your Cascade Bungalow provides a heightened experience in an adult-only setting (for guests 21+). Inside you’ll find an inviting sunken living room with a cozy fireplace, high ceilings, a modern bedroom area, a workstation, coffee and tea bar, a spacious bathroom, and expansive windows that offer stunning views and open to a personal patio. Outside, soak in your private enclosed hot tub made for two.

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!

Charming Modernized 1938 Ranch Home

Enjoy a taste of ranch life in this modernized 1938 home. Located on a large, peaceful lot in downtown Prineville, guests can walk to many amenities. The picture windows offer a view of colorful sunsets, deer and quail from both the covered porch and the living room. Comfortably furnished and tastefully decorated, this home reminds guests of the cowboy lifestyle of yesteryear. Conveniences include kitchen appliances, dishwasher, WiFi, smart TV, Blue Ray/DVD player, fans, and ample parking.

Bitterroot Butte | Prineville Reservoir

This spacious and absolutely stunning home is the perfect getaway. Take in the breathtaking views of the Prineville Reservoir and surrounding mountains. The Prineville Reservoir was recently designated as an International Dark Sky area making this the perfect place to stargaze. Easy access to the lake for summer watersports, fishing, hiking, biking and more! Access to public lands for hiking etc. right from the property! *4x4 or all wheel drive is required to access this property*

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.

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!

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.

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.

Brasada Ranch | High Desert Modern Luxury | Sauna

Relax with stunning mountain views from a spacious patio with a fire pit and seating, or unwind in a private sauna off the primary suite. Cook like a pro in a chef’s like kitchen with a professional stove, chef's grade ventilation, full cookware, dinnerware, a bar with complete glassware for wine, spirits, and cocktails, and a wine cooler. Fully equipped for travelers seeking comfort, convenience, and memorable moments.