House vacation rentals in Crook County

A deck area features a small round table with two chairs, illuminated by string lights overhead. A barbecue grill is positioned nearby, with falling leaves scattered across the wooden deck. The entrance of the casita shows a door with multiple windows, enhancing its inviting appearance.

4.82 out of 5 average rating, 79 reviews

La Casita de Main Street - Central OR's Cottage

Stylish & cozy casita perfect for your extended stay in Central Oregon. Interior recently updated, yet embracing some of its original quirkiness, Our Southwest inspired home provides all amenities; inc. full kitchen, washer/dryer, large shaded & fenced yard with deck to enjoy. BBQ, patio table and lounge chairs. Conveniently located within walking distance to Crooked River access, Crook County Fairgrounds, Meadow Lakes Golf Course and Downtown Prineville. Sorry, no short term stays at this time.

4.88 out of 5 average rating, 26 reviews

Home in Powell Butte

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.

A spacious covered outdoor seating area features comfortable sofas surrounding a central fire pit. The serene lake view is framed by tall trees, while sun loungers are positioned nearby on the deck. The area is illuminated by natural light and provides an inviting atmosphere.

4.98 out of 5 average rating, 133 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

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.

4.73 out of 5 average rating, 48 reviews

Charming Modernized 1938 Ranch Home

Enjoy a taste of ranch life in this modernized 1938 home. Located on a large, peaceful lot in downtown Prineville, guests can walk to many amenities. The picture windows offer a view of colorful sunsets, deer and quail from both the covered porch and the living room. Comfortably furnished and tastefully decorated, this home reminds guests of the cowboy lifestyle of yesteryear. Conveniences include kitchen appliances, dishwasher, WiFi, smart TV, Blue Ray/DVD player, fans, and ample parking.

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.

4.83 out of 5 average rating, 78 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! ❤️

The bedroom features a spacious bed with decorative pillows and a quilted coverlet. A wooden headboard adds a rustic touch, while a map of Europe adorns the wall. A comfortable rocking chair and bedside lamps provide soft lighting, enhancing the room's cozy ambiance.

5 out of 5 average rating, 63 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!

A bright dining area is surrounded by large windows, offering expansive views of the Prineville Reservoir and nearby mountains. A rustic wooden table is set for six, complemented by comfortable chairs and a cozy seating arrangement in the adjacent living space.

4.96 out of 5 average rating, 57 reviews

Bitterroot Butte | Prineville Reservoir

This spacious and absolutely stunning home is the perfect getaway. Take in the breathtaking views of the Prineville Reservoir and surrounding mountains. The Prineville Reservoir was recently designated as an International Dark Sky area making this the perfect place to stargaze. Easy access to the lake for summer watersports, fishing, hiking, biking and more! Access to public lands for hiking etc. right from the property! *4x4 or all wheel drive is required to access this property*

Superhost

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.

4.81 out of 5 average rating, 88 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!

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.

4.98 out of 5 average rating, 159 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.

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.

5 out of 5 average rating, 9 reviews

LaFollette by Stahancyk House

This Queen Anne cottage in Oregon's Ochoco Valley, built in the early 1900s, has a rich history in the sheep and wool industry. Built by Thomas H. Lafollette and Margaret J. Allen, the house was passed down through generations. After Hazel Sullivan's passing, the house fell into disrepair. A recent restoration has revitalized it, addressing foundation issues, lead paint remediation, and restoring original features. The updated living space blends the past with the present.

Two horses are seen grazing peacefully in a lush, green field surrounded by tall trees. A fenced area is visible with a water trough placed nearby, providing a tranquil outdoor setting.

4.82 out of 5 average rating, 11 reviews

Yikes place

Relax with the whole family at this peaceful place to stay. Our little town offers lots of things to do In the summer Horse races, rodeos, fair, rock hounds, Pee wee rodeos I could go on. You will be close to Prineville reservoir, Ochoco reservoir, Ochoco mountains. Great for Hunters , fisherman , boaters. In town we have a theater, museum , antique stores, Restaurants, Community pool, Parks for the kids with a splash pad , golfers have 2 golf course.

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.