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Family-friendly holiday rentals in Crook County

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Top-rated family-friendly rentals in Crook County

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious bedroom is furnished with a wooden sleigh bed topped with neutral linens and a decorative black blanket. Two bedside lamps illuminate the room. A stylish folding screen provides privacy, and large windows offer scenic views of the valley.
Guest suite in Prineville

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).

Indoor spacesKitchenAir conditioning

4.94 out of 5 average rating, 288 reviews
Top guest favourite
A cozy living area is presented with a dark sofa adorned with colorful cushions. A guitar and artwork are displayed on the walls. Natural light filters through a large window, complemented by houseplants and warm lighting from a standing lamp.
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.

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 119 reviews
Superhost
A modern kitchen features a sleek island with four wooden bar stools arranged around it. Open shelving displays dishware and decorative items. Ambient lighting is provided by two pendant lights hanging above the island, and stainless steel appliances complement the clean, minimalist design.
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.

Indoor spacesFamilyCleanliness

4.84 out of 5 average rating, 294 reviews
Top guest favourite
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.
Home in Prineville

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! ❤️

FamilyKitchenAmenities

4.87 out of 5 average rating, 110 reviews
Guest favourite
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.
Home in Prineville

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!

Indoor spacesKitchenWalkability

4.82 out of 5 average rating, 100 reviews
Top guest favourite
A cozy tiny home with wooden exterior is set against a backdrop of lush greenery. A fire pit sits in the foreground, surrounded by open grass. A deck is visible, featuring a grill and seating area that invite outdoor relaxation.
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.

KitchenFamilyHospitality

4.94 out of 5 average rating, 172 reviews
Top guest favourite
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.
Home in Prineville

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.

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 218 reviews
Top guest favourite
Two Adirondack chairs are positioned on a patio, facing a stunning sunset over distant mountains. A small table is located between the chairs, accompanied by a flower pot. The sky is painted with hues of pink, orange, and purple, creating a serene atmosphere.
Guest suite in Powell Butte

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!

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 267 reviews
Guest favourite
Home in Prineville

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

FamilyIndoor spacesValue

4.96 out of 5 average rating, 108 reviews
Guest favourite
Home in Prineville

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!

FamilyKitchenGrill

4.83 out of 5 average rating, 30 reviews
Guest favourite
Home in Prineville

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!

Indoor spacesKitchenQuiet

4.9 out of 5 average rating, 42 reviews
Guest favourite
Home in Prineville

Funky Bungalow in The Heart of Downtown Prineville

Warm. Cozy. A little funky. J Tree is a pet-friendly 2-bedroom, 1-bath stay right in the heart of downtown Prineville, Oregon. This older vintage-inspired bungalow has personality — colorful decor, unique art, a funky layout, and a comfortable feel that makes it an easy Central Oregon home base. Dream. Journey. Rest.

Air conditioningSleep qualityLocation

5.0 out of 5 average rating, 7 reviews

Popular amenities for Crook County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
The exterior view of a spacious two-story house is captured from above, surrounded by trees and shrubs. A grey roof covers the home, featuring multiple gabled sections. The yard includes a patio area, with a barbecue setup, adding to the outdoor entertainment options.
Home in Powell Butte

Brasada Getaway! Golf, Hot Tub, Theater Room!

FamilyIndoor spacesLocation

4.71 out of 5 average rating, 7 reviewsThe front exterior of the house showcases large windows that create a bright and open atmosphere. A sheltered patio area is visible, featuring seating and a fire pit area surrounded by logs. Tall trees are in the background, enhancing the natural setting.
Home in Prineville

Country Getaway

FamilyIndoor spacesHospitality

4.75 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Powell Butte

The Nest at Brasada Ranch

KitchenFamilyBathroom

5.0 out of 5 average rating, 9 reviews
Superhost
Home in Powell Butte

Peaceful Brasada Oasis | Hot Tub & Views

KitchenFamilySleep quality

5.0 out of 5 average rating, 5 reviews
Superhost
The exterior of a spacious luxury retreat showcases natural wood siding and stone accents, framed by a serene sunset sky. The driveway leads to a three-car garage with large glass-paneled doors, complemented by strategically placed trees and landscaped grounds.
Home in Powell Butte

Two Saddle Estate | Brasada Ranch | 5200 SF!

FamilyIndoor spacesSleep quality

4.64 out of 5 average rating, 14 reviews
Guest favourite
Home in Powell Butte

Sunset Ridge Ranch at Brasada Ranch

KitchenIndoor spacesNearby

4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Powell Butte

Brasada Ranch Elegance | Hot Tub| Bocce| Ping Pong

FamilyNearbyHot tub

5.0 out of 5 average rating, 5 reviews
Superhost
A hot tub is positioned on a wrap-around deck, inviting relaxation with a bubbling surface. Surrounding greenery and scenic views of the landscape enhance the tranquil setting, while blue skies and distant structures create a sense of openness.
Cabin in Powell Butte

Brasada Ranch Cabin 21 Mtn & Golf Views Hot Tub

Indoor spacesFamilyQuiet

4.75 out of 5 average rating, 16 reviews

Family- and pet-friendly home rentals

Guest favourite
Camper van/Motorhome in Prineville

Grand Escape

KitchenIndoor spacesSleep quality

4.88 out of 5 average rating, 72 reviews
Guest favourite
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.
Home in Prineville

The One Above the Rest w/Game Room

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 86 reviews
Superhost
An open living area is presented, featuring a round dining table with two chairs and a cozy sofa. A comfortable queen bed is positioned in the background. Natural light filters through two windows, illuminating the warm wooden accents and soft neutral tones throughout the space.
Farm stay in Powell Butte

Romantic Ranch Oasis near Bend, Redmond,Prineville

Indoor spacesKitchenQuiet

4.93 out of 5 average rating, 27 reviews
Guest favourite
Home in Powell Butte

Panoramic views!

FamilyKitchenView

5.0 out of 5 average rating, 36 reviews
Guest favourite
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.
Home in Prineville

Charming Modernized 1938 Ranch Home

KitchenIndoor spacesPets

4.75 out of 5 average rating, 53 reviews
Guest favourite
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.
Home in Prineville

LaFollette House by Stahancyk House

Indoor spacesFamilyNearby

5.0 out of 5 average rating, 13 reviews
Guest favourite
Guest house in Prineville

The Thoroughbred Suite 2bd 1 bth

FamilyAmenitiesComfort

5.0 out of 5 average rating, 5 reviewsA rustic covered kitchen area features a wooden table with benches, accented by natural greenery. A charcoal grill is positioned nearby, and whimsical decor hangs from the ceiling. The surroundings showcase open space with scattered trees, presenting a natural and inviting wilderness cooking experience.
Tent in Deschutes County

Aurora Outfitters NW Klondike

QuietGetting aroundLocation

4.86 out of 5 average rating, 7 reviews

Family-friendly home rentals with a pool

Superhost
Home in Powell Butte

Brasada Ranch Retreat • Hot Tub + Resort Access

KitchenViewAccess

5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Powell Butte

Brasada Ranch | 2 Full Suites | On Golf Course

HospitalityCheck-inAmenities

5.0 out of 5 average rating, 5 reviews
Home in Powell Butte

Juniper Ranch - Golf Cart Included | Sleeps 10

FamilyIndoor spacesLayout

4.89 out of 5 average rating, 80 reviews
Home in Powell Butte

Brasada Golf Retreat | 3 King En Suites + Bunk

FamilyWalkabilityNearby

5.0 out of 5 average rating, 3 reviewsAn open-concept living area is showcased, featuring a large sectional sofa and a wooden coffee table. A stone fireplace adds warmth, while a mounted TV is positioned above it. The kitchen is visible in the background, with wooden cabinetry and appliances.
Cabin in Powell Butte

Mountain-View Cabin Near Trails in Powell Butte!

FamilyKitchenHospitality

5.0 out of 5 average rating, 8 reviews
Luxe
The spacious studio layout features a cozy sunken living area with a wrap-around couch and a modern gas fireplace. A king-size bed is positioned above on a raised platform, complemented by wooden cabinetry and warm lighting. Large windows provide natural light throughout the space.
Bungalow in Powell Butte

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

ViewHospitalityPets

4.9 out of 5 average rating, 10 reviewsA tranquil cabin is nestled among desert vegetation, featuring a welcoming porch with seating. The exterior showcases a combination of wood and stone materials under a sloped roof, illuminated by warm evening light. Surrounding brush and trees add to the rustic charm of this inviting retreat.
Cabin in Powell Butte

Brasada Ranch, Decks, Patio, Resort Amenities!

FamilyKitchenCheckout

4.63 out of 5 average rating, 8 reviews
Superhost
A spacious deck features comfortable lounge seating arranged around a fire pit, with scenic views of the surrounding landscape. The deck's wooden flooring complements the rustic charm of the high ceiling and beams overhead, while a hot tub is visible in the corner.
Home in Powell Butte

Hot Tub, Fire Pit, Views | Brasada Ranch Community

FamilyIndoor spacesHospitality

4.71 out of 5 average rating, 55 reviews