Vacation rentals in Crook County

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Top-rated vacation rentals in Crook County

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Guest favorite

Guest suite in Prineville

4.93 out of 5 average rating, 219 reviews

Artsy Guest House Nestled in the Rimrock

This property is truly an oasis from the hustle and bustle of city life. When you arrive, the massive rimrock wall will greet you; it is home to abundant wildlife (owls, deer, coyotes oh my). Shrouded by silence, the trill of frogs will put you to sleep. Mornings start with sunrise over the Ochoccos and full views of the valley and the crooked river at its base. Take a hike at Smith Rock, visit the Painted Hills or find yourself headed to town (Bend: 45 min, Prineville: 10 min, Redmond: 25 min).

Oct 23 – 30

G$24,191 GYD per night

Guest favorite

Guesthouse in Powell Butte

4.9 out of 5 average rating, 63 reviews

Juniper Bunkhouse - newly renovated!

Enjoy either a relaxing or adventurous getaway located on a rustic ranch. Gorgeous views of Smith Rock, Grizzly Mountain and Cascade Mountains can be seen anywhere on the ranch as it is situated at the base of the Powell Butte. Feel free to take a short, easy hike to the edge of the property where there is a bistro table to sit at and admire the Sisters mountains as well as Mt. Jefferson and Mt. Washington. Walk route map provided at the time of stay. We are excited to share the views with you!

Mar 15 – 22

G$27,507 GYD per night

Guest favorite

Farm stay in Prineville

4.93 out of 5 average rating, 370 reviews

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.

Sep 2 – 9

G$21,641 GYD per night

Guest favorite

Cottage in Prineville

5.0 out of 5 average rating, 36 reviews

~The Quail Run Cottage~

**Please read full description & look at all pictures to ensure it’s the right fit for your needs** This little gem is in the prime location. It’s in the country but 5 minutes from the town of Prineville. It offers beautiful open views and nature all around. Take a load off & soak in the private hot tub & enjoy the scenery, it will not disappoint. Enjoy watching the quail run around the property along with other wildlife. Lots of room for trailers ** Please note- There is no washer/dryer**

Aug 25 – Sep 1

G$29,533 GYD per night

Guest favorite

Home in Prineville

4.98 out of 5 average rating, 95 reviews

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!

Jan 24 – 31

G$198,056 GYD per night

Guest favorite

Townhouse in Prineville

4.94 out of 5 average rating, 106 reviews

High Desert Oasis

We would like to welcome you to our bountiful urban farmstead. This duplex is located in an established neighborhood of Prineville and located 4 blocks from the Barnes Butte Park which host miles of hiking and biking trails exemplifying the Great American West. Downtown breweries and the Ochoco Creek Park with trails are just minutes away. The Prineville Reservoir and the Ochoco Reservoir, as well as the Ochoco National Forest are just thirty minutes from the front door.

May 14 – 21

G$36,075 GYD per night

Guest favorite

Guesthouse in Mitchell

4.94 out of 5 average rating, 333 reviews

Painted Hills at Thompson Creek House, Mitchell Or

Kick back, relax and enjoy our home on 80 acres of big sky, fresh air and great scenery . Just 10 miles from Painted hills! Your room has an adjoining private tv and eating area with a separate entry from the main part of the house. Microwave , fridge ,coffee maker provided with beverages and snacks abundantly stocked. Also a grill set up for grilling out. Continental style breakfast each morning of your stay. Let us be your gateway to Wheeler County. Bob & Leslie

Oct 15 – 22

G$23,139 GYD per night

Guest favorite

Apartment in Prineville

5.0 out of 5 average rating, 22 reviews

Log Cabin Hideaway

Your family or group will be comfortable in this spacious and unique space! This cabin apartment features a full kitchen with an extra refrigerator, living room, dining area and lots of floor space to spread out and make yourselves at home. Its a very family and pet friendly space with a futon bed that’s great for kids. There are toys in the closet, a playground right outside and multiple streaming options for children and adults. Its only an 8 minute drive to town.

Sep 2 – 9

G$22,768 GYD per night

Guest favorite

Guest suite in Powell Butte

4.97 out of 5 average rating, 144 reviews

Panoramic Mountain View Oasis

Your high desert sanctuary awaits. Enjoy breathtaking panoramic mountain views from your second floor apartment, stargaze in the hot tub, cozy up outside by the wood-burning fireplace, and so much more! Only 2 miles from Brasada Ranch, convenient for weddings and events. Close to world-famous Smith Rock, centrally located between Bend, Redmond, and Prineville for a myriad of outdoor activities. Forget your worries in this serene and peaceful place!

Apr 15 – 22

G$39,219 GYD per night

Guest favorite

Guest suite in Prineville

4.98 out of 5 average rating, 59 reviews

Trendy apartment in the heart of Prineville

Please read the entire listing description before booking. We want you to enjoy your stay with us! Our home was built in 1938 as part of FDR's New Deal. It is a beautiful old home with a spacious, daylight basement that has been converted into this fun, stylish, comfortable space. Fun fact: the blacksmith work in our home was done by O.B. Dawson, the head blacksmith at the Historic Timberline Lodge on Mt. Hood which was another New Deal project.

Aug 29 – Sep 5

G$19,065 GYD per night

Guest favorite

Home in Prineville

5.0 out of 5 average rating, 23 reviews

Millers' Misfit Farm

Millers' Misfit Farm welcomes you to the farm. The space was originally built into the house as a mother in law's quarters. There is a separate entrance with porch, full kitchen with pantry, one bedroom with queen sized bed and a walk in closet, one queen hide a bed couch in the living room, and one bathroom with shower. In the yard is a seasonal firepit. Come stay with us and enjoy the beauty of Central Oregon!

Jun 30 – Jul 7

G$26,023 GYD per night

Guest favorite

Home in Prineville

4.95 out of 5 average rating, 21 reviews

Cute and Updated Downtown Duplex

Enjoy a stay in downtown Prineville. Walking distance from grocery stores, restaurants, city parks, and shopping. 2 Bedrooms, one full bathroom. Recently beautifully updated. Play set in the fully fenced back yard, with a deck. Parking off of the street with a 4 car driveway. Master bedroom has a California King bed and the second room has a Full size bed. Access to free weights and a row machine.

Dec 28 – Jan 4

G$22,815 GYD per night