Holiday rentals in Crook County

Guest suite in Prineville

4.94 out of 5 average rating, 247 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).

4.98 out of 5 average rating, 56 reviews

Cabin in Prineville

Cabin in the Ochocos

Our cabin/guest house is located on 32 acre forested property next to the main house and is a perfect base camp for hikers, bikers, hunters, dark sky and winter sport enthusiasts. It overlooks Upper McKay Valley, is one mile from the north entrance of Ochoco National Forest and 10 minutes north of downtown Prineville. Ideal for 2 but can accommodate 4 people to share the amenities of a small scale fully equipped home. Amazing views with farm animals to round out the country living experience.

4.98 out of 5 average rating, 44 reviews

Loft in Prineville

The Howdy Hideaway

Experience vintage cowboy charm in our centrally located Prineville retreat! Our place is about an hour from the infamous Painted Hills. This cozy apartment offers everything you need for a weekend getaway or an extended stay, and doesn't include a cleaning fee! Located on a quiet street and within a 10 minute walk to downtown, restaurants, parks, and shops. Explore local attractions, and the amazing outdoors of central Oregon, or relax in our charming space. Book now for a memorable getaway!

Superhost

Home in Powell Butte

4.81 out of 5 average rating, 16 reviews

Comfortable and quiet guest house

Come and enjoy the beauty of Central Oregon while you stay in this adorable, detached guest quarters in the hills of Powell Butte. This high desert property has views of some of the Cascades as well as Smith Rock. The guesthouse sits behind the main home on 5 acres for privacy. It is centrally located between Bend, Redmond and Prineville for a wide range of outdoor activities including easy access to Brasada Ranch and Smith Rock. Enjoy bird watching, wildlife, walks and incredible sunsets.

4.98 out of 5 average rating, 123 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!

Superhost

Loft in Prineville

4.84 out of 5 average rating, 246 reviews

Gateway to Painted Hills! Downtown Prineville Loft

Completely renovated historic building in downtown Prineville. Walk to everything. Light filled, loft-style apartment featuring modern decor & furnishings. Great home base for your trip to Central Oregon. The Painted Hills are just less than an hour drive. Smith Rock is 25mins away. Designated bike storage available inside the loft. NOTE: The loft is on the 2nd floor of a walk-up building. There are approx. 25 steps leading up to the apartment and there is no elevator in the building.

4.86 out of 5 average rating, 66 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! ❤️

4.79 out of 5 average rating, 81 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!

Guest house in Prineville

5 out of 5 average rating, 10 reviews

Discovery Loop Landing

Hello and welcome to our brand new modern, all-inclusive 700 sq. ft. apartment with private entrance, free private parking, peaceful and safe area located in a "dark sky" neighborhood to best enjoy the beautiful Central Oregon night skies. Choose this home for an easy transition.. Turn-key and stocked with everything you need to make this your new home. Cannot wait to meet you! Ask me about monthly payments ! Please note the address reading 935 B - this Is a two unit property.

4.94 out of 5 average rating, 143 reviews

Tiny home in Prineville

Tiny Pine house in the Ochocos at Wine Down Ranch

Cozy, country tiny home with deck, fire pit, views of meadows, and Ochoco National Forest. Interact with the horses, cattle, and dogs. Serene space with beautiful views of the Cascade mountains. Dark sky certified. View the Milky Way, many constellations, and a few galaxies. Located on 2100 acre Ranch, which is 11 miles from Prineville and 1 mile from the National Forest. Many outdoor activities are available - hiking, mountain biking, snowshoeing, birding, and much more.

5 out of 5 average rating, 106 reviews

Cottage in Prineville

~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. Located 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. **Please note- There is no washer/dryer/oven**

4.99 out of 5 average rating, 141 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.

Holiday rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Crook County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Crook County

Place to stay in Prineville

4.75 out of 5 average rating, 28 reviews

The Pine~ Movie Theater & Apartment

AleksaRating, 5 stars4 weeks ago

The stay was one of a kind! We have never stayed in a movie theater! After the theater was closed to the public for the day we were able to go into the upstairs cinema and watch music videos and have a dance party with the kids it was an unforgettable experience and we had so much fun! The main bedroom was spacious enough to fit 2 of the 4 air mattresses provided and the whole family had a sleepover! Thank you so much!

Home in Powell Butte

4.96 out of 5 average rating, 24 reviews

1 BR w Sauna, Hot Tub, 5 min to Brasada

StephenRating, 5 stars10 months ago

Location was 5 minutes from Brasada Ranch. We had the bottom floor of the house to ourselves. It was very quiet and peaceful.

Luxe

Bungalow in Powell Butte

5 out of 5 average rating, 3 reviews

Luxury Bungalow w Hot Tub at Brasada Ranch (21+)

MeredithRating, 5 stars3 months ago

This was a beautiful get-away. The condo was absolutely stunning with ALL the amenities; heated bathroom floor, black out shades, amazing views, lovely linens, and the list goes on! I highly recommend this place and am excited to return soon.

Chalet in Prineville

4.83 out of 5 average rating, 23 reviews

Lake front home on the Prineville reservoir

ChristopherRating, 5 stars1 week ago

Very enjoyable location. We went for a fishing trip and had enough parking for two pickups with 20 foot boats on trailers. Everything in the house worked. We had a small issue with the internet on check in but, Jim was very responsive and resolved the issue in short order. House is located around the corner of a state park with a well maintained boat launch that has courtesy dock. We could be on the water within 10 minutes of the house.

Guest suite in Prineville

4.57 out of 5 average rating, 7 reviews

Bella Blue

DavidRating, 5 stars3 days ago

A great spot to stay exactly as portrayed in the ad, clean, comfortable, and cozy

Private room in Prineville

4.96 out of 5 average rating, 77 reviews

Little Bit Ranch . " Little bit of this and that"

JenniferRating, 5 stars8 months ago

I think the only thing for us wpuld have been an updated tv situation but other then that just what we were looking for. Thanks again lorrie

Private room in Prineville

4.91 out of 5 average rating, 181 reviews

Riverbend House

JaneRating, 5 stars4 weeks ago

Barbara is a gracious thoughtful host; her townhouse is clean and comfortable, filled with mementos of a full life. We enjoyed returning from a day of driving and hiking to our cozy comfortable room.