Family-friendly holiday rentals in Jefferson County

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Family · Kitchen · Bathroom

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.

Kitchen · Indoor spaces · Quiet

Villa Solé, the Perfect Fall/Winter Getaway!

Bring your group to Villa Solé, an unforgettable destination in sunny Central Oregon. Groups LOVE this unique place for its unbeatable mountain views, peaceful vibes, fun activities indoors and out, and ABUNDANCE of space to spread out and relax. Send us a message to inquire about our special winter rates! Your group will love the deluxe coffee bar, wood-burning stove that churns out major heat in cold weather, cozy blankets everywhere, and location for enjoying all that Central Oregon offers.

Family · Indoor spaces · Long stay

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

Kitchen · Indoor spaces · Sleep quality

Volcano Outlook

Large, 16X20 glamping tent on an insulated platform, above the Deschutes River. Walk to the Steel Head Falls in 30 minutes. Tent has 1 queen size bed, and a futon, that can be made into a bed. The tent has electricity and cold water inside the tent. Porta potty is behind the tent. Local/Day trips to hiking, biking, fishing, golfing or kayaking in Central Oregon. Beautiful views of the Cascade Mountains. Matching platform for relaxing and cooking outside, with hot shower located behind.

Kitchen · Indoor spaces · Sleep quality

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Family · Indoor spaces · Comfort

Madras Oak House

This cozy 2-bedroom, 2-bathroom house is the perfect retreat for your stay in the heart of Madras. Full access to the entire 926 sqft house. Enjoy unopposed mountain views and short driving distances to downtown, restaurants, Willow Canyon trail, Sahalee Park, Deschutes River, Cove Palisades and Smith Rock State Parks. **Due to severe allergies, no smoking on premises and no pets are allowed. If you bring a pet, you will be asked to leave and will be charged $200 for extra cleaning.**

Family · Kitchen · Outdoor spaces

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Indoor spaces · Family · Pets

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.

Family · Indoor spaces · Quiet

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

Indoor spaces · Kitchen · Laundry

Steelhead Falls Log Cabin

Enjoy a restful time in our waterfront log cabin along the Deschutes River. Location is perfect for watching wildlife, fly fishing, quiet relaxation, and has easy access to hiking and rock climbing at Smith Rock and Lake Billy Chinook. Steelhead Falls is a a short hike away. Bend and Sisters are near. Unfortunately, we cannot accommodate even small weddings. We recommend access to AWD vehicle with either chains or snow tires in winter. Dog friendly- sorry, no cats.

Indoor spaces · Family · Wi-Fi

High Desert Retreat

Escape to our luxuriously converted school bus in the high desert and enjoy off grid living with all the comforts of home. Features AC & heat, full kitchen, queen bed, hot shower, composting toilet, complimentary coffee and fresh linens & towels. Take in wide-open skies, peaceful high desert views, and a nearby chicken coop for a touch of country charm. Well-behaved dogs are welcome (must be chicken-friendly).

Kitchen · Indoor spaces · Nearby