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.

Prineville Reservoir! Lake front, walk to beach!

Amazing new listing from Superhost with OVER 500 FIVE STAR REVIEWS! Located above the Prineville Reservoir with a 180° view of the lake and mountains. Only a 2 minute walk to the beach, and we provide kayaks, paddle boards, and beach gear for you! Gather around the gas fire pit and enjoy our premium stargazing; this area received the rare International Dark Sky Park designation, bringing visitors from all over the world! Family reunion, friend gathering, or small event; this is your spot!

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.

Lakefront Retreat | Ochoco Lake

Welcome to Lakefront Retreat on the shores of Ochoco Lake. This peaceful 4BR/2BA lakefront home sleeps 10 and offers direct access for kayaking, fishing, and swimming. Relax on the deck with sunset views, spot deer, antelope, geese, and hawks, and enjoy stargazing under clear Central Oregon skies. Cozy comforts include A/C, Wi-Fi, smart TV, and a full kitchen. Quick access to the Ochoco Mountains and Painted Hills for day-trip adventures. Professionally managed by Desert Sage Rentals LLC.

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.

Ochoco Valley Cottage

A peaceful private guest cottage tucked into the foothills of the Ochoco Mountains. Enjoy wide open views, star-filled skies, and frequent wildlife right outside your door. Just 45 minutes from the Painted Hills and close to Walton Lake and Big Summit Prairie. Clean, cozy, and family-friendly with a unique loft sleeping area accessed by a ship ladder — perfect for couples, small families, and travelers wanting a quiet Central Oregon getaway.

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.

Panoramic views!

Escape to your own 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.