Vacation rentals in Crooked River

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Top-rated vacation rentals in Crooked River

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Top guest favourite
The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.
Home in Terrebonne
4.98 out of 5 average rating, 965 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!

Top guest favourite
Home in McKenzie Bridge
4.99 out of 5 average rating, 113 reviews

Wrens Nest, river, golf, fish, hike, raft, relax!

The Wren's Nest located in the magical Willamette National forest. Quiet Riverfront privacy, quality kitchen for that cozy home feel. Snuggle up on the couch or go enjoy nature. Relax on the wrap around deck while watching the Mckenzie river, lovely creek or stargazing! An acre of trees & wildlife provides a tranquil space any time of year. Nearby rafting, Tokatee golf, Mckenzie River trail, Belknap hot springs, Sahalie Falls, Clear Lake, Hoodoo ski resort, Loloma Lodge. Relax, this is a ReSet~

Guest favourite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne
4.9 out of 5 average rating, 330 reviews

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!

Superhost
The exterior of the modern farmhouse is visible, featuring a covered porch with two red Adirondack chairs. The structure is surrounded by gravel, with a pathway leading to a set of stairs. Natural landscaping includes a small tree and various shrubs.
Home in Terrebonne
4.95 out of 5 average rating, 202 reviews

Smith Rock Hideout - Cascade mountain views

The Hideout is a cozy and convenient base camp for climbers, hikers, trail runners, digital nomads, and anyone wanting to relax and explore the beauty of Central Oregon. Just 8 minutes to Smith Rock! Take in the views of the Cascade mountains and farmland beyond while relaxing on the covered porch. The Hideout is my personal semi-rural retreat. While away, I’m happy to share it with outdoor enthusiasts who enjoy creature comforts after a day of getting after it outdoors. Longer stays welcome!

Top guest favourite
Two wooden Adirondack chairs are positioned near the water’s edge, overlooking the flowing McKenzie River. Lush greenery surrounds the area, with trees providing a natural canopy and enhancing the sense of seclusion in this tranquil setting.
Cabin in McKenzie Bridge
5 out of 5 average rating, 194 reviews

McKenzie Bridge River House near Sahalie Falls

Drive down a long private road, set off of the HWY, to find a riverfront cabin amidst the lush Willamette National Forest. As you wind through the driveway you will find a sanctuary for relaxation, recreation, and comfort. A trail from the back deck will lead you down to the bank of the emerald waters of the McKenzie River. The McKenzie River Trail parallels the property, and is accessed from the private road to the cabin. The property has a campground setting, with river and forest views.

Top guest favourite
A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.
Home in Terrebonne
4.97 out of 5 average rating, 368 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.

Top guest favourite
Tiny homes in Bend
4.9 out of 5 average rating, 315 reviews

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

We are opening up our Aframe to host some visitors to Bend. This Aframe was originally built for the Rajneeshpuram, in Wasco county Oregon in the early 1980's. If you are not familiar with this interesting piece of Oregon history, we recommend you watch the documentary Wild Wild Country on Netflix. It is fascinating. Its a small little dwelling, we have a king sized Mattress in it (no bed frame due the space limitations), with easy access to a bathroom and shower in our home.

Top guest favourite
A studio cabin is positioned on a deck overlooking a canyon, surrounded by native plants. Two wooden chairs are placed on the deck, providing a space to absorb the expansive mountain views in the distance. The structure features a large window reflecting the evening light.
Cabin in Culver
4.9 out of 5 average rating, 270 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.

Top guest favourite
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.
Home in Terrebonne
4.97 out of 5 average rating, 504 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.

Guest favourite
A view from the lodge path shows a wraparound deck overlooking the Marsupial rock formations. Dense trees provide shade, while the high desert landscape is dotted with shrubs and rocky terrain. The clear sky enhances the natural beauty of the surrounding area.
Home in Terrebonne
4.94 out of 5 average rating, 168 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.

Top guest favourite
A vintage camper is seen under a clear night sky, adorned with string lights that create a soft glow. A campfire ring is positioned in the foreground, surrounded by natural stones. Nearby, a shower house can be seen, also illuminated, with outdoor seating available.
Camper/RV in Terrebonne
4.97 out of 5 average rating, 152 reviews

Tin Can Ranch

Welcome to Tin Can Ranch! Kick your legs up and enjoy the sunset at Tin Can Ranch where your worries drop away like the leaves in Autumn! Our cozy Vintage Yellowstone "Tin Can" camper is nestled in it's own corner of our 5 acre property located in Terrebonne, OR just a 10 minute drive from Smith Rock State Park and within an hour of the very best outdoor adventures in Central Oregon! Next to the camper is the shower house/bathroom with an outdoor washing sink.

Guest favourite
A private outdoor area features a hot tub surrounded by string lights, creating a cozy ambiance. A wooden table displays a bottle of sparkling wine with two glasses and a small potted plant, inviting relaxation and enjoyment in nature.
Cabin in Bend
4.92 out of 5 average rating, 227 reviews

Eco cabin near Bend: sauna, spa, king bed, EV plug

Tucked away on a quiet acre in Three Rivers, our cabin is a cozy, eco-friendly basecamp for Central Oregon adventures. Soak in the hot tub after a day on the trails, warm up in the barrel sauna, or gather by the fire pit under the stars. Inside, you’ll find knotty pine, a full kitchen, WiFi, and thoughtful eco-friendly touches. 30 min to Bend and Mt. Bachelor, 15 min to Sunriver — and far from the noise.

Popular amenities for Crooked River vacation rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Jefferson County
  5. Crooked River