Holiday rentals with outdoor seating in Crook County

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.

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

THIS IS A RESORT-MANAGED LISTING, GIVING YOU ACCESS TO ALL BRASADA RANCH'S LUXURY AMENITIES Your Cascade Bungalow provides a heightened experience in an adult-only setting (for guests 21+). Inside you’ll find an inviting sunken living room with a cozy fireplace, high ceilings, a modern bedroom area, a workstation, coffee and tea bar, a spacious bathroom, and expansive windows that offer stunning views and open to a personal patio. Outside, soak in your private enclosed hot tub made for two.

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!

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.

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!

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.

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!

The One Above the Rest w/Game Room

Discover the allure of Central Oregon in this captivating downtown Prineville home. Perfect for families and professionals, this charming house offers a prime location near restaurants and shops. Enjoy a game room with a pool table, darts, and arcade machines. Marvel at stunning sunsets and stargazing. Conveniently situated for exploring Bend, Smith Rock, and the Painted Hills. Your ultimate hub for adventure and relaxation.

Juniper Ridge Retreat

Peace, tranquility, and memory making await you at Juniper Ridge Retreat. This area has received the rare International Dark Sky Park designation bringing visitors from all of the world for premium stargazing. Amazing views of Prineville Reservoir and surrounding wilderness from all rooms and the wrap around deck allow you to take in the beauty of this unique area.