Holiday houses 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, 54 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, 43 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!

4.98 out of 5 average rating, 120 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, 241 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, 65 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! ❤️

5 out of 5 average rating, 43 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. The apartment is kept critter free for those of you with allergies. Come stay with us and enjoy the beauty of Central Oregon!

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, 102 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, 140 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.

4.88 out of 5 average rating, 280 reviews

Tiny home in Mitchell

COPPINI’S Creekside Camp, Painted Hills

Coppini Creekside Camp is “glamping” at its best. Our cabin sits away from it all at the bend of Thompson Creek. Nesteled amongst beautiful juniper trees. A fire pit ,outdoor cooking station and a cooler with ice waiting for your beverages and perishables.Inside is a comfy queen bed and loft with a single mattress. Cabin has bathroom with camp shower and toilet. Tent available for guests that want more of the camping experience. Come, relax and have a super experience.

Superhost

4.75 out of 5 average rating, 8 reviews

High Desert Retreat | Prineville

This cozy High Desert Retreat located in Prineville comfortably sleeps 4 adults. Enjoy a full kitchen, Wi-Fi, smart TV, and outdoor spaces with seating/BBQ. Centrally located near Prineville Reservoir, Ochoco National Forest, Ochoco Reservoir, Barnes Butte (and more) for hiking, fishing, rockhounding, sight-seeing and much more. Perfect for families and outdoor lovers looking to explore the High Desert! Professionally Managed by Desert Sage Rentals LLC

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Other great holiday rentals in Crook County

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.

4.93 out of 5 average rating, 393 reviews

Farm in Prineville

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

AngelaRating, 5 stars1 week ago

Mary’s bunkhouse was perfect in every way. This property is an amazing slice of heaven away from the hustle & bustle of everyday life. Beautiful place to unwind & relax. I can’t say enough good things about Wine Down Ranch & Mary is the best, will definitely by back soon!

Luxe

Bungalow in Powell Butte

5 out of 5 average rating, 3 reviews

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

MeredithRating, 5 stars2 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.

Home in Powell Butte

4.96 out of 5 average rating, 49 reviews

The Luxurious Ranch Life

CelesteRating, 5 stars7 months ago

A beautiful home in a beautiful location! Our large group fit comfortably in this home with plenty of space for everyone. The kitchen is amazing and well stocked for cooking meals. The outdoor kitchen and sitting area are amazing! Our schedule did not allow us to use any amenities of the resort.

Private room in Prineville

4.96 out of 5 average rating, 77 reviews

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

JenniferRating, 5 stars7 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 stars2 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.

4.67 out of 5 average rating, 3 reviews

Country Getaway

JimRating, 5 stars1 month ago

In short the house was stunning. It was like walking into a magazine and if it hasn't been featured in one it should be. The post and beam construction was stunning and at the same time all the wood was warm and welcoming and the art and furnishing compliment it perfectly. While just a quarter mile from the quiet road we might as well have been in another world. Quiet, cozy and happy. And the kitchen... it had everything a cook could ask for. It was the perfect getaway for my family and friends and to a person we all want to come back. Finally, our host Amy was a delight. Friendly, responsive and extremely accommodating. I've stayed in many places throughout the west and this was hands down the best experience I've had.