Vacation rentals in Crooked River

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Crooked River

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Prineville

4.93 out of 5 average rating, 218 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).

Nov 17 – 24

R2,198 ZAR per night
Guest favorite

Apartment in Redmond

4.98 out of 5 average rating, 423 reviews

Smith Rock View 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.

Nov 29 – Dec 6

R2,700 ZAR per night
Guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 801 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!

Sep 16 – 23

R6,981 ZAR per night

Popular amenities for Crooked River vacation rentals

Other great vacation rentals in Crooked River

Guest favorite

Guest suite in Terrebonne

4.86 out of 5 average rating, 217 reviews

High Desert Adventure Suite

May 6 – 13

R1,724 ZAR per night
Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 164 reviews

Smith Rock Gardens

Jun 1 – 6

R3,868 ZAR per night
Guest favorite

Cabin in Terrebonne

4.98 out of 5 average rating, 268 reviews

Steelhead Falls Log Cabin

Mar 5 – 12

R6,771 ZAR per night
Guest favorite

Guest suite in Terrebonne

4.95 out of 5 average rating, 307 reviews

Comfy & Cozy!

Jul 22 – 29

R1,962 ZAR per night
Guest favorite

Guesthouse in Bend

4.96 out of 5 average rating, 570 reviews

Little Sister

Sep 6 – 13

R1,845 ZAR per night
Guest favorite

Tiny home in Bend

4.95 out of 5 average rating, 102 reviews

The Sunset Bungalow, cozy, private and sweet.

Aug 3 – 10

R2,159 ZAR per night
Guest favorite

Cabin in La Pine

4.95 out of 5 average rating, 193 reviews

Cozy Forest Cabin w/ Sauna & Hot Tub!

Oct 21 – 28

R3,208 ZAR per night
Guest favorite

Guest suite in Powell Butte

4.96 out of 5 average rating, 140 reviews

Panoramic Mountain View Oasis

Mar 15 – 22

R3,631 ZAR per night
Guest favorite

Home in Redmond

4.81 out of 5 average rating, 512 reviews

Immaculate, Cozy Home in the Heart of Downtown

Mar 20 – 27

R1,817 ZAR per night
Guest favorite

Guest suite in Redmond

4.93 out of 5 average rating, 246 reviews

Spacious and Private Suite in Central Oregon!

Aug 23 – 30

R1,668 ZAR per night
Superhost

Cabin in Culver

4.86 out of 5 average rating, 36 reviews

Cabin on The Rim

Jan 6 – 13

R1,745 ZAR per night
Guest favorite

Guest suite in Madras

4.96 out of 5 average rating, 78 reviews

Cozy daylight basement, guest suite!

Apr 29 – May 6

R1,803 ZAR per night

Destinations to explore

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