Holiday rentals in Crooked River Ranch

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Top-rated holiday rentals in Crooked River Ranch

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Guest favourite

Guest suite in Prineville

4.93 out of 5 average rating, 242 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).

Guest favourite

Rental unit in Redmond

4.97 out of 5 average rating, 484 reviews

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A huge covered deck with magnificent views will make you feel right at home. Get your trip started off right with a gorgeous sunrise over Smith Rock.

Guest favourite

Home in Terrebonne

4.98 out of 5 average rating, 857 reviews

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!

Guest favourite

Cabin in Bend

4.99 out of 5 average rating, 462 reviews

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

Guest favourite

Home in Terrebonne

4.97 out of 5 average rating, 230 reviews

Pointe of Blessing with hot tub and canyon views

We hope you will enjoy our Pointe of Blessing. We feel our canyon perch is a gift from God-just 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. Prepare to relax unwind and enjoy spectacular sunrises and moonrises.

Guest favourite

Home in Terrebonne

4.98 out of 5 average rating, 183 reviews

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

Guest favourite

Tiny home in Redmond

5 out of 5 average rating, 233 reviews

Tranquil Views, Close to Smith Rock, Country Cozy

The Tiny House at Aspen View Farm is just what you need! Great location for exploring beautiful Central Oregon - Smith Rock is only 15 min away. On a unique 14 acre farm, relax and retreat with tranquil Cascade Mountain and country views, say hi to Roo the farm dog, and watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, a/c, heated floors & more! Please read full listing before booking so there are no surprises :)

Guest favourite

Guest house in Terrebonne

4.98 out of 5 average rating, 134 reviews

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

Guest favourite

Cabin in Culver

4.91 out of 5 average rating, 108 reviews

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.

Guest favourite

Guest suite in Terrebonne

4.96 out of 5 average rating, 344 reviews

Comfy & Cozy!

Great place for a work-from-home alternative or get-away. Relax in a separate, quiet suite with dedicated, private entrance and parking. Enjoy the spacious 560 sq ft suite, with comfy queen bed, stocked kitchenette, large living area, and full bathroom. The essentials are here + more! With a stunning view of the Cascade Mountain Range, you can enjoy the beauty of a colorful sunset, and maybe see some wildlife! Only 5 minutes to Smith Rock, grocery, & restaurants.

Guest favourite

Guest house in Terrebonne

4.9 out of 5 average rating, 262 reviews

Compound Coziness...Terrebonne Guesthouse

Come and join us in gorgeous Central Oregon! The guesthouse is part of our 5 acre property that we live on with our two friendly dogs. Your house has a private fenced in area, but you are welcome to explore the entire property and watch gorgeous sunsets of the Cascade Range. This house provides a queen bed in one room, and a double and twin bunk bed in the second room. A full kitchen and washer/dryer gives you the convience to make this your home during your visit.

Guest favourite

Home in Terrebonne

4.96 out of 5 average rating, 431 reviews

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 mine and I live on site with my daughters family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering or checking the NEW spa. We are open for a 2 night minimum. Checkout time is strict to allow for cleaning and sanitizing.