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

Apartment in Redmond

4.98 out of 5 average rating, 427 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 15 – 22

G$28,875 GYD per night

Guest favorite

Tiny home in Mitchell

4.91 out of 5 average rating, 111 reviews

Cozy Coyote Camp in Mitchell Oregon

Coyote Camp is a one room cabin located off Highway 26, on " Lost Coyote Lane" in Mitchell, Oregon.. Located 10 minutes from the Painted Hills... The cabin offers a quiet place, to relax, and enjoy all the trees and surrounding nature.There are lots of places to go for walks, or just enjoy a quiet breakfast, on the deck. We offer a Queen size bed, small kitchen with a refrigerator microwave toaster Keurig coffee pot, pods are provided . Please follow directions sent with check in info.

Oct 12 – 19

G$22,945 GYD per night

Guest favorite

Farm stay in Prineville

4.93 out of 5 average rating, 370 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

With 2100 acres nestled against the Ochoco NF, our ranch is a family-owned working ranch. Dark sky certified. Amazing view of the Milky Way and stars. Scenic meadows, managed forest lands, and rock vistas make up the landscape. Enjoy the slow-paced country lifestyle in an authentic ranch setting with horses, cows and dogs. Guests are welcomed and encouraged to enjoy the whole property. Many hiking areas and views to explore. Usual snowy winters make great fun for cc skiing and snow shoeing.

Jun 3 – 10

G$21,623 GYD per night

Guest favorite

Home in Terrebonne

4.97 out of 5 average rating, 165 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.

Aug 10 – 17

G$47,419 GYD per night

Guest favorite

Guest suite in Bend

4.98 out of 5 average rating, 218 reviews

Portal to the Cascades

An attached, private guest suite in a unique lovely home. Rural, beautiful, open 5 acres with breathtaking views of the Three Sisters. On a private dead end road surrounded by thousands of acres of Forest Service and BLM land. Feels like miles from nowhere, yet just 15 minutes to Sisters and 30 minutes to downtown Bend. Very peaceful and quiet. Come and relax, explore the area by bicycle or by foot, watch birds, stargaze, and simply commune with nature. A truly special property. DCCA # 742778

Oct 4 – 11

G$22,414 GYD per night

Guest favorite

Apartment in Mitchell

4.94 out of 5 average rating, 515 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.

Oct 29 – Nov 5

G$37,648 GYD per night

Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 120 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.

Apr 6 – 13

G$79,196 GYD per night

Guest favorite

Tiny home in Redmond

4.99 out of 5 average rating, 187 reviews

Tranquil Views, Close to Smith Rock, Country Cozy

The Tiny House at Aspen View Farm is your next special getaway! Great location for solo travelers or couples exploring beautiful Central Oregon - Smith Rock 15 min away. On a unique 14 acre farm setting, relax and retreat with tranquil Cascade Mountain and country views, plus watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, heated floors & more! Please read full listing before booking so there are no surprises :)

Dec 11 – 18

G$34,625 GYD per night

Guest favorite

Home in Mitchell

4.91 out of 5 average rating, 216 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.

Aug 4 – 11

G$42,640 GYD per night

Guest favorite

Cabin in Bend

4.99 out of 5 average rating, 429 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. 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 .

Sep 30 – Oct 7

G$18,675 GYD per night

Guest favorite

Guesthouse in Mitchell

4.94 out of 5 average rating, 333 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

Aug 30 – Sep 6

G$23,120 GYD per night

Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 135 reviews

Smith Rock Hideout - Cascade mountain views

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

Nov 27 – Dec 4

G$30,226 GYD per night