Pet-friendly holiday rentals in Crook County

Dog-Friendly Ranch Cottage w/ Yard ~ 13 Mi to Bend

A peaceful, private retreat awaits in rural Bend at the Honest Dog Ranch! ‘The Bunkhouse’ is a 3-bedroom, 1-bath cottage nestled beside the Oregon Badlands Wilderness, offering direct access to marked trails, natural sites and abundant wildlife. The ranch is rich in history and art, with authentic architecture and one-of-a-kind paintings. Enjoy Cascade Mountain views and serene surroundings at this high-desert hideaway, only 30 minutes from the breweries, boutiques and eateries in Downtown Bend!

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 | 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!

Aurora Outfitters NW Klondike

Get away from it all and sleep under the stars. This is camp site on 20 acres of private land and can easily fit large groups or several RVs. No hook ups but we offer complete privacy with only two camp sites that are completely separated for a wonderful wilderness experience. Both sites have an outhouse, covered kitchen space and dining area and charcoal grill to use. In addition there is a common area with horseshoe pits, library/game room, cozy seating areas and shower house.

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.

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 | 2 King Suites | Beautiful Views

Watch golfers tee off on the infamous hole #9 from your own private hot tub at Brasada Ranch! Fast internet, 2 King suites w/their own private work areas & mini-fridges, a private hot tub, and all the amenities. Just a quick walk to golfing, swimming, and much more that Brasada Ranch has to offer!