Kid-friendly 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, 45 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, 124 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!

4.94 out of 5 average rating, 52 reviews

Modern Brasada Ranch 5 Bed Luxury Home w/ Firepit

Enjoy a modern well appointed five bedroom luxury home in Brasada Ranch. The home sleeps 12 across 5 bedrooms and is perfect for entertaining large groups. Brasada Ranch was recently voted "PNW's #1 Resort." *Please note that this home has add mandatory resort fees that will be collected prior to your stay. The rates are: Jan - April: $40/per guest per night. May - Sept: $65/per guest per night. Oct - Dec: $40/per guest per night. All holiday time periods: $65/per guest per night.

4.84 out of 5 average rating, 246 reviews

Loft in Prineville

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.

4.87 out of 5 average rating, 67 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! ❤️

4.94 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, 107 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.

4.88 out of 5 average rating, 282 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.

4.82 out of 5 average rating, 11 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

Holiday rentals for every style

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Kick off your hiking boots at these rustic lodgings

Hotels

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Popular amenities for Crook County family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Kid-friendly house rentals

4.72 out of 5 average rating, 47 reviews

Charming Modernized 1938 Ranch Home

JenniferRating, 5 stars1 month ago

Fantastic! Very happy with my experience here!

5 out of 5 average rating, 3 reviews

Brasada Ranch | Stunning Views | Couple's Getaway

BrookRating, 5 stars4 months ago

Perfect Space for Creativity & Podcast Recording! We couldn’t have asked for a better place to stay! This Airbnb wasn’t just a home—it was an inspiring, well-thought-out space that elevated our entire experience. We used it as a recording studio for our podcast, and it couldn’t have been more perfect. The acoustics were excellent, the layout allowed for a smooth workflow, and the quiet surroundings made it ideal for focused recording sessions. The natural light and stylish decor created a great atmosphere, both for creative energy and for capturing stunning behind-the-scenes content. Beyond that, the hosts were incredibly thoughtful, ensuring we had everything we needed. The space was spotless, comfortable, and felt like a true retreat after long days of recording. If you’re looking for a place that blends functionality with inspiration—whether for work, creativity, or just relaxation—this is the one. We’ll absolutely be back!

4.79 out of 5 average rating, 81 reviews

Lake front in Prineville~

PaulaRating, 5 stars1 month ago

I was very impressed with the home. We all slept like we were at home. Beautiful location. My husband fished every day. Loved that they accepted dogs since we have a service dog that must travel with us. I hope to return.

4.65 out of 5 average rating, 31 reviews

Clint by AvantStay | Golf Course, Pool & Hot Tub

CraigRating, 5 stars1 month ago

We had an amazing stay at Brasada Ranch. The house was very spacious and was an excellent pick for our family retreat. Upstairs game room was a great location for the kids to play. AvantStay was very responsive and the house was exactly as described. Would definitely love to stay at one of their properties again in the future.

4.96 out of 5 average rating, 26 reviews

Beautiful Ranch Home w/ Cascade Mountain View

NitikaRating, 5 stars9 months ago

Lisa and Matt’s place was perfect in all terms. We were looking for a place where we could just hang out with beautiful surroundings and spend quality time with our adult kids before moving out of country. Their place was tastefully done, with all amenities you can think of, everything from the linens to the appliances were of finest quality. We enjoyed walking around their property, watching sunrise and sunset on their patio, playing board games and making some good memories. It was blissful. They go above and beyond to make their guest welcome with wine and snacks and fresh eggs from their coup, chocolates, berries and yogurt, most of which we enjoyed. And special treats for our puppy.

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.

4.89 out of 5 average rating, 9 reviews

The Lookout at Brasada Ranch

MaryRating, 5 stars4 months ago

What a beautiful and clean home. The view was amazing! The description of the home and pictures were accurate. The outdoor patio and fire pit were great! The pool, hot tubs and recreation area were an added bonus but we could have easily just stayed and the home and played games around the nice large dining table. Great family get away with many laugh and great memories! Thank you