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.

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! ❤️

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.

LaFollette by Stahancyk House

This Queen Anne cottage in Oregon's Ochoco Valley, built in the early 1900s, has a rich history in the sheep and wool industry. Built by Thomas H. Lafollette and Margaret J. Allen, the house was passed down through generations. After Hazel Sullivan's passing, the house fell into disrepair. A recent restoration has revitalized it, addressing foundation issues, lead paint remediation, and restoring original features. The updated living space blends the past with the present.

Cozy, stylish Bungalow in Downtown Prineville

Warm and Cozy bungalow in the heart of downtown Prineville, OR — the perfect Pet-friendly Central Oregon getaway. Walk to local shops, relax or work remotely in a warm, vintage-inspired space designed for comfort and ease. ✔ Comfortable beds with quality linens ✔ Natural light ✔ Fully stocked kitchen + Coffee Station ✔ Fast WiFi ✔ Smart TV ✔ Easy self check-in ✔ Free parking ✔ Washer & dryer ✔ Fenced backyard with doggie door Dream. Journey. Rest.

The Juniper House | Prineville

Welcome to The Juniper House, a charming and spacious 4-bedroom, 2.5-bath home, ideal for family get-togethers, leisure and resting between adventures. Conveniently situated near Prineville's public parks, you'll have easy access to playgrounds, craft and farmers markets, and the scenic Ochoco Creek. You'll also be centrally located with access to shopping, dining, outdoor adventures and more! Professionally managed by Desert Sage Rentals LLC

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!

Brasada Ranch Cabin 21 Mtn & Golf Views Hot Tub

Welcome to Cabin 21, a beautifully updated 2-bedroom, 2-bathroom vacation retreat located at the entrance of the gated Brasada Ranch community. With only being a 2-3 minute walk to resort amenities and unobstructed views of the golf course and Cascade Mountains, this thoughtfully designed home offers a true luxury escape in the heart of Central Oregon.

Incredible Cabin Incredible Views Dark Sky Area

Views to die for in Central Oregon. Beautiful rustic (but very nice) cabin/home situated on 20 ACRES overlooking lake and river. 17 miles SE of Prineville. You will feel totally secluded, but just a mile down the hill to state park and boat ramp.