Pet-friendly holiday rentals in Crook County

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.

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.

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! ❤️

Bitterroot Butte at 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*

Lake front in Prineville~

Lake front privacy...Fish, Swim, water ski, kayak right here in your own back yard. Bring your horses to the Ochoco wilderness. Hike or rock climb at Smith Rock, take a day shopping in Bend or just have a relaxing time away enjoying Prineville! Please know the lake is a reservoir and depending on snowfall to completely fill the lake. Late summer the lake recedes because of the use of irrigation in the Prineville farm territory. Please use the boat ramp when the lake is low!

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.

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.

High Desert Vista Home: Modern Trailside Retreat

Perched on Central Oregon's edge, this sleek 3 Bedroom home sleeps 6 (pet-friendly, 2 dogs <50lbs). Barnes Butte trails from backyard—hike, bike, views! Vaulted ceilings, big windows with vistas. Gas fireplace, modern kitchen with island. King primary with shower, 2 queens, 2 baths, laundry. Fenced yard, covered patio for sunsets & stars. Near downtown, Reservoir, Smith Rock, Bend, Ochoco. Adventure awaits!

Windflower Farm Stable Loft 2 BR apartment

Expansive, elevated views of our farm, neighboring buttes and ranches. Windflower specializes in biodiverse, regenerative agriculture: flowers, vegetables, fruit, herbs, beneficial insect havens, and horses. You'll find road biking for miles and mountain biking just 5 min. away in the BLM, Reynolds Pond, and Badlands Wilderness. We're only 20 minutes to Bend's many shops and restaurants.

Panoramic views!

Escape to your own private paradise! This getaway offers breathtaking panoramic views, an oversized patio with outdoor heating, and an unforgettable stargazing experience. Whether you're here for a weekend of relaxation or an adventure, you'll find everything you need to unwind and recharge.

Brasada Ranch High Desert Luxury Cabin

Enjoy the beautiful scenery of the Cascade Mountains and Juniper trees from your private hot tub at Brasada Ranch! Fast internet, 2 private work areas, a private hot tub, and all the amenities. Just a quick walk to golfing, swimming, and much more that Brasada Ranch has to offer!