Vacation rentals in Crooked River Ranch

4.98 out of 5 average rating, 898 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!

4.97 out of 5 average rating, 153 reviews

A wooden staircase leads down from a spacious deck, lined with wooden railings. The surrounding landscape features greenery and mature trees, offering a natural setting. Sunlight casts shadows on the deck, creating a serene outdoor atmosphere.

Apartment in Redmond

Large Mountain View Suite on Quiet Acreage

Quiet rural location just a few miles from town on the rimrock above a small canyon. Enjoy a panoramic view of the Cascades from a spacious studio apartment that is comfortable and uncluttered. Features a roomy bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. Additional fee for each pet. Roll-away twin bed on req. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 mi

Superhost

A winding river flows through a rugged landscape characterized by rocky cliffs and sparse vegetation. The banks are lined with patches of greenery, and yellow-hued foliage indicates the changing seasons. The scene captures the natural beauty of the high desert terrain.

Guest suite in Terrebonne

4.84 out of 5 average rating, 274 reviews

High Desert Adventure Suite

Our guest suite provides a comfortable home-base for anyone looking to explore the high desert. We are just a 5 minute drive from Smith Rock State Park and we provide a parking pass for guests to use. Our neighborhood is quiet and our home is on a cul-de-sac. The suite has two rooms; one is a spacious designated bedroom with a queen bed, the other doubles as a second bedroom and living space with a daybed and trundle bed. The suite has it's own private patio and a bit of a view of Smith Rock.

4.96 out of 5 average rating, 181 reviews

A bright bathroom features a white sink below a round wooden mirror. The walls are painted a deep grey, with white beadboard paneling across the lower half. A cozy living space is visible through the open door, showcasing a spacious bed and soft natural light.

Home in Redmond

Downtown Redmond Loft

Experience the joy of our space! We've poured our hearts into making sure you feel perfectly at home and cared for. Located in the vibrant heart of downtown Redmond, our house is a tranquil oasis nestled amidst the beauty of Dry Canyon's parks and the bustling energy of breweries, restaurants, food carts, and shops. 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend. We're delighted to share our stylish home – welcome to your unforgettable stay! Cheers, JoHanna

4.97 out of 5 average rating, 505 reviews

A spacious outdoor deck is furnished with two Adirondack chairs facing a circular fire pit. A panoramic view of distant mountains and valleys is framed by a railing, showcasing the landscape under clear blue skies.

Apartment in Redmond

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 daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

4.98 out of 5 average rating, 283 reviews

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.

A modern kitchen features sleek countertops and dark cabinetry, complemented by large windows that frame expansive views of Smith Rock. Natural light floods the space, highlighting a variety of kitchen appliances and a telescope positioned by the window.

4.99 out of 5 average rating, 248 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.

5 out of 5 average rating, 248 reviews

A river cascades over rocky ledges, creating small waterfalls that flow into a wider, vibrant body of water. Vegetation including sparse trees and shrubs can be seen along the rocky banks, adding contrast to the textured landscape. The surrounding terrain is rugged and dry.

Tiny home in Redmond

Close to Smith Rock, Mountain View, Country Charm

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 :)

4.98 out of 5 average rating, 160 reviews

The entrance features a vibrant coral door framed by stone accents, leading into the guest house. A small welcome mat is placed before the door. Red Adirondack chairs are positioned nearby, and green and gray plants add a natural touch to the patio area.

Guesthouse in Terrebonne

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.

4.91 out of 5 average rating, 173 reviews

A studio cabin is positioned on an elevated area overlooking a vast canyon. The structure features a simple exterior with large windows, allowing natural light to fill the space. The surrounding landscape includes rugged terrain and sparse vegetation under a softly colored sky at dusk.

Cabin in Culver

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.

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

4.96 out of 5 average rating, 456 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 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.

Large windows dominate the wall, offering a clear view of the Marsupial rock formations and the surrounding trees. A comfortable seating area features a sofa and a coffee table adorned with a decorative item, all illuminated by warm sunlight.

4.95 out of 5 average rating, 156 reviews

Fallen Snag Lodge next to Smith Rock State Park

One mile from Smith Rock State Park & 30 minutes from Bend, Fallen Snag Lodge will be your very own private nature preserve. A wrap around deck faces the Marsupial rock formations & Crooked river, with lounge chairs set to view hawks, turkey vultures & eagles during the day & for stargazing at night. Ideal for couples or a family wanting to get away from it all in a beautifully appointed, comfortable lodge set in central Oregon's magnificent high desert landscape.

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Other great vacation rentals in Crooked River Ranch

5 out of 5 average rating, 6 reviews

A rustic deck chair is positioned on a wooden railing, overlooking the expansive Crooked River Canyon at sunset. The silhouette of a distant mountain is visible against a colorful sky, complemented by the winding road below and surrounding greenery.

Cabin in Terrebonne

The Rim House, Timeless & Serene

BrittanyRating, 5 stars1 week ago

Absolutely fabulous hosts. Beautiful views and adorable wildlife (marmot and a pair of quail). Views of Mount Hood in the distance. We felt right at home at the end of a long travel day. Check out these newer hosts; they are awesome!

An aerial view of the interior space showcases an open floor plan, highlighting various living areas. Natural light floods through large windows, illuminating the wooden floors and rustic furnishings. Distinct zones for dining and relaxation are visible, with a cozy seating arrangement positioned around a central area.

4.93 out of 5 average rating, 41 reviews

Rock Ridge

KassenaRating, 5 stars5 months ago

This is the second time I have stayed at Adams place. It amazing. This is Terrebone, so be aware that the location is not close to Bend. We enjoyed visiting Smith Rock and star gazing at night. The property is far from Bend and Redmond so it has some great night skies. This was a great place for a gathering of friends and family. The kitchen is well stocked with pots, pans, and decent knives (rare find.) Living area is great for gathering at night to chat, play games, and snacks. Beds were all really comfy, even the bunk beds. Adam is a great host who on both visits has been incredibly responsive. If you are looking for a great stay w great views I highly recommend.

4.89 out of 5 average rating, 72 reviews

A bright kitchenette is equipped with a refrigerator, microwave, and toaster oven, alongside shelves displaying various glassware. A small sink is positioned next to a countertop, with stylish decor enhancing the space. The area is complemented by warm wooden flooring and natural light.

Cottage in Redmond

Blossom Cottage Studio

LorettaRating, 5 stars3 weeks ago

Great place to stay for a quick overnight trip

5 out of 5 average rating, 20 reviews

A rustic wooden board displays a freshly baked loaf of bread, partially sliced. A bouquet of vibrant flowers, featuring purple, orange, and green blooms, is arranged nearby. The bread is wrapped in white paper, tied with twine, showcasing a tag for a local bakery.

Place to stay in Sisters

Convenient Quant Space in Sisters

SarahRating, 5 stars1 month ago

Beautiful stay in such a lovely location! It was just outside town and we enjoyed how peaceful and quiet the neighborhood was. The interior was beautiful and had all the amenities we needed. They even baked us some delicious homemade sourdough that we enjoyed with the butter and jam that they provided with our tea! It was chilly while we were there but the mini split and little space heater kept us very cozy and comfortable! We loved being about to bring our dog along and that is was pet friendly. Being able to close the gate so that our pup that we had with us to be able to run around a bit was excellent. We didn't get a chance to use it but loved that we had the option to enjoy some time in the chairs outside by the solo stove. Would 10/10 recommend and would absolutely stay here again! Thank you!

Superhost

A serene outdoor scene features two lounge chairs positioned beside a tranquil pond. The area is surrounded by lush green grass and trees, with smooth rocks lining the water's edge. The clear blue sky reflects softly on the calm surface of the water.

Yurt in Sisters

4.88 out of 5 average rating, 42 reviews

JJR Private Yurt with full bathroom, mountain

TinaRating, 5 stars1 month ago

The Sisters Yurt was absolutely perfect. The one negative was....I called specifically to see if there was a fire pit. I was told there was so we picked up firewood. There is NO fire pit near the yurt. That was not a make or break for us though. The view of the 3 Sisters is amazing!! The quiet surroundings was exactly what we needed. The bed was comfortable, the kitchen was fully equipped. We will be back, we loved the property and the yurt.

4.89 out of 5 average rating, 300 reviews

A panoramic view captures the rugged terrain of a canyon, showcasing towering rock formations and a river winding through the landscape. Sparse vegetation and a clear blue sky enhance the natural beauty of the high desert setting.

Cottage in Terrebonne

Quiet central Oregon desert retreat with a view!

CharlesRating, 5 stars1 week ago

We stayed the last days in May and the first days in June 2025. The place was clean with everything needed to relax, enjoy our stay and also do our own cooking. We sat outside at sunset and watched the stars come out. We hiked at Smith Rock State Park and visited Bend and Redmond. It was a great stay and I'm recommended it to friends and hope to be back next year.

4.94 out of 5 average rating, 65 reviews

A modern bathroom countertop showcases a sleek gray soap dispenser alongside a small white dish holding a bar of soap. Towels are neatly rolled and stored in a basket, enhancing the organized and tidy appearance of the space.

Cabin in Terrebonne

Mountain View Cabin near Smith Rock - Pet-Friendly

ReaganRating, 5 stars1 week ago

Maria has done a wonderful job of preparing this home for an extremely comfortable stay. The views are spectacular, and we cannot wait to come back!