Painted Hills vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Painted Hills

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

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Guest favorite

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 favorite

Home in Terrebonne

4.98 out of 5 average rating, 860 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 favorite

Cabin in Bend

4.99 out of 5 average rating, 466 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 favorite

Home in Terrebonne

4.97 out of 5 average rating, 236 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 favorite

Rental unit in Mitchell

4.94 out of 5 average rating, 579 reviews

Off Grid Ranch's Apt Back side of Painted Hills.

This 1,600 sq ft ground level apartment with garden area and separate entrances has a full bath and complete kitchen. Queen bed in one bedroom, plus a crib in semi private area and another large bedroom has two queen beds with bookcases separating beds. Hiking, fishing, hunting, horseback riding, swimming or floating the John Day River, and available roads for ATV riding. On our 320 acres you can relax on the decks, take in the views of our amazing landscape, watch the birds and wildlife.

Guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 188 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 favorite

Home in Mitchell

4.91 out of 5 average rating, 236 reviews

Spacious & Modern Painted Hills Vacation Home

Located just a few miles from the stunning Painted Hills, one of the 7 Wonders of Oregon, our house is spacious and open with modern amenities and relaxing outdoor spaces. We have completely updated the house with all new furniture and beautiful design touches making it the perfect place to stay when exploring the Painted Hills & John Day Fossil Beds! Our Mitchell, Oregon vacation home is a short walk to Main Street which has a brewery, several restaurants, a market & a gas station.

Guest favorite

Cabin in Culver

4.91 out of 5 average rating, 113 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 favorite

Tiny home in Prineville

4.93 out of 5 average rating, 132 reviews

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.

Guest favorite

Guesthouse in Mitchell

4.94 out of 5 average rating, 391 reviews

Painted Hills at Thompson Creek House, Mitchell Or

Kick back, relax and enjoy our home on 80 acres of big sky, fresh air and great scenery . Just 10 miles from Painted hills! Your room has an adjoining private tv and eating area with a separate entry from the main part of the house. Microwave , fridge ,coffee maker provided with beverages and snacks abundantly stocked. Also a grill set up for grilling out. Continental style breakfast each morning of your stay. Let us be your gateway to Wheeler County. Bob & Leslie

Guest favorite

Guest suite in Powell Butte

4.96 out of 5 average rating, 189 reviews

Panoramic Mountain View Oasis

Your high desert sanctuary awaits. Enjoy breathtaking panoramic mountain views from your second floor apartment, stargaze in the hot tub, cozy up outside by the wood-burning fireplace, and so much more! Only 2 miles from Brasada Ranch, convenient for weddings and events. Close to world-famous Smith Rock, centrally located between Bend, Redmond, and Prineville for a myriad of outdoor activities. Forget your worries in this serene and peaceful place!

Guest favorite

Cabin in Kimberly

4.97 out of 5 average rating, 259 reviews

Stellar Cabin

Wake Up to Wedding Cake! Stellar Cabin can be your private hideaway. Soak in the wood fired hot tub and gaze up at a blanket of stars. Cook a steak on the grill, make dinner in the fun cook shack and sit around and watch evening come. John Day Fossil Beds are close by. Hike Blue Basin, swim in the river or dig for fossils! We are out of range for most cell service, but it's close by. Wifi available at host house if needed! And pets are welcome!