House vacation rentals in Crook County

A cozy living area features a wooden cabinet housing books and a television. A small dining table with two chairs is positioned by a window, while a colorful area rug adds warmth to the tile floor. A door leads to another room.

4.87 out of 5 average rating, 106 reviews

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! ❤️

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A single-story home is presented with a sloping roof and a welcoming front porch. A two-car garage is visible on the left side, while the surrounding lawn offers a natural, grassy area. Mountains and a lake are seen in the background under a clear blue sky.

4.82 out of 5 average rating, 96 reviews

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!

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A cozy master bedroom features a log queen bed with a green quilt. Two bedside tables with lamps provide soft lighting. A fan is positioned nearby, and a doorway leads to a bathroom area, emphasizing the spacious layout.

4.97 out of 5 average rating, 207 reviews

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.

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A spacious living area features pastel-colored sofas, arranged to facilitate conversation. Decorative curtains frame the windows, enhancing natural light. An intricately patterned rug covers the wooden floor, while a dining table is positioned in the background, providing a sense of connection between the two spaces.

5 out of 5 average rating, 13 reviews

LaFollette House 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.

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The exterior of a modernized 1938 home is displayed, featuring a gray facade with white trim. A covered porch extends from the main entrance, surrounded by a gravel driveway and landscaped areas. Large windows allow for natural light, and trees add greenery to the property.

4.75 out of 5 average rating, 52 reviews

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 views of colorful sunsets, deer and quail. Comfortably furnished and tastefully decorated, this home reminds guests of a cowboy lifestyle of yesteryear. Home features ceiling fans, portable fans, coffee maker, dishwasher, microwave, WiFi, smart TV, Blue Ray/DVD player, fans, and ample parking.

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Superhost

Home in Powell Butte

5 out of 5 average rating, 3 reviews

Brasada Ranch Retreat • Hot Tub + Resort Access

Welcome to Hat Rock Loop by AvantStay. This secluded Powell Butte retreat pairs modern comfort with sweeping Central Oregon views, making it perfect for couples or solo travelers. Spend your days exploring Brasada Ranch, Bend, or nearby trails, then return for hot tub soaks, alfresco dinners, and quiet nights under the stars. ♨️ Private hot tub with high desert views 🏊 Access to Brasada Ranch resort amenities 🍳 Fully equipped kitchen, smart TV + in-home laundry

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A game room is displayed, featuring a green felt pool table with a set of balls arranged on the table. A dartboard is mounted on the wall adjacent to a small lamp and seating. Natural light enters through a window, illuminating the space.

4.98 out of 5 average rating, 83 reviews

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.

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4.96 out of 5 average rating, 103 reviews

Court St. Cottage | Downtown Prineville

Welcome to Court Street Cottage, a one-of-a-kind and cozy home nestled in the heart of Downtown Prineville, Oregon! Walk to shops, restaurants and coffee houses. Located just a stone's throw away from the historic Crook County Courthouse, this charming cottage is the perfect gateway to the breathtaking beauty of the Ochoco Mountains, Painted Hills and the Crooked River Backcountry. Managed by Desert Sage Rentals LLC

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4.81 out of 5 average rating, 26 reviews

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!

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4.96 out of 5 average rating, 23 reviews

An inviting outdoor area features a built-in gas fire pit surrounded by stone seating, with flames glowing brightly. The expansive house is visible in the background, showcasing large windows that emit soft, warm light, set against a twilight sky.

Home in Powell Butte

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.

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4.89 out of 5 average rating, 37 reviews

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!

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