House holiday rentals in Crook County

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.

Yikes place

Relax with the whole family at this peaceful place to stay. Our little town offers lots of things to do In the summer Horse races, rodeos, fair, rock hounds, Pee wee rodeos I could go on. You will be close to Prineville reservoir, Ochoco reservoir, Ochoco mountains. Great for Hunters , fisherman , boaters. In town we have a theater, museum , antique stores, Restaurants, Community pool, Parks for the kids with a splash pad , golfers have 2 golf course.

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.

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.

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.

The Lookout at Brasada Ranch

Welcome to the Lookout! This expansive home boasts panoramic Cascade Mountain views, a sprawling lawn, patio & large built in gas fire pit. A covered terrace runs along the back where you can enjoy dinner, drinks and dramatic sunsets with friends & family. Inside find voluminous ceilings, a dramatic stone fireplace, open kitchen, large pantry & wine closet. Features 5 BR & a 2nd story bunk room.

Creekside Cottage

Welcome to peaceful Creekside Cottage. One minute walk to beautiful downtown Prineville. Close to dining, groceries and gas. One step away from the bike path, and a stone's throw away from tranquil Ochoco Creek! Private, yet centrally located. Ample off street parking. Sleeps 6 adults, full kitchen, laundry. The home boasts beautiful artwork created by lovely local artist Kristine Cooper!

Sunset Ridge Ranch at Brasada Ranch

Welcome to Sunset Ridge Ranch at Brasada Ranch—where western rustic charm meets modern luxury. Take in sweeping desert and Cascade Mountain views from your own private hot tub. Enjoy a beautifully appointed, spacious kitchen ideal for cooking and gathering, challenge friends to a game of pool, or head to the garage for cornhole and laid-back fun.