Vacation rentals in Painted Hills

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Top-rated vacation rentals in Painted Hills

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Top guest favorite

A spacious bedroom is furnished with a wooden sleigh bed topped with neutral linens and a decorative black blanket. Two bedside lamps illuminate the room. A stylish folding screen provides privacy, and large windows offer scenic views of the valley.

Guest suite in Prineville

4.94 out of 5 average rating, 259 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).

Superhost

A spacious outdoor patio area is framed by wooden beams with climbing vines overhead. A barbecue grill and a round fire pit are visible on the ground, surrounded by potted plants. Outdoor seating includes metal chairs and a table, offering a relaxing spot to enjoy the surroundings.

Apartment in Mitchell

4.93 out of 5 average rating, 643 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, 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 around outside fireplace, take in the views of our amazing landscape, watch the birds and wildlife.

Guest favorite

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, 920 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

A sandy path winds through a landscape filled with various green shrubs and trees, leading toward distant hills under a clear blue sky. The gentle slopes of the hills display a mix of earthy tones, creating a serene natural setting.

Tiny home in Mitchell

4.91 out of 5 average rating, 192 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.

Top guest favorite

A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.

Cabin in Bend

4.99 out of 5 average rating, 522 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.

Top guest favorite

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, 311 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.

Superhost

A modern kitchen features a sleek island with four wooden bar stools arranged around it. Open shelving displays dishware and decorative items. Ambient lighting is provided by two pendant lights hanging above the island, and stainless steel appliances complement the clean, minimalist design.

Loft in Prineville

4.84 out of 5 average rating, 253 reviews

Gateway to Painted Hills! Downtown Prineville Loft

Completely renovated historic building in downtown Prineville. Walk to everything. Light filled, loft-style apartment featuring modern decor & furnishings. Great home base for your trip to Central Oregon. The Painted Hills are just less than an hour drive. Smith Rock is 25mins away. Designated bike storage available inside the loft. NOTE: The loft is on the 2nd floor of a walk-up building. There are approx. 25 steps leading up to the apartment and there is no elevator in the building.

Top guest favorite

A spacious living area features large glass windows that provide views of the surrounding landscape, including trees and open fields. Comfortable seating with brown leather upholstery is arranged around a central coffee table. Natural light fills the room, highlighting the modern design.

Home in Terrebonne

4.99 out of 5 average rating, 278 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

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

4.89 out of 5 average rating, 212 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 favorite

A cozy tiny home with wooden exterior is set against a backdrop of lush greenery. A fire pit sits in the foreground, surrounded by open grass. A deck is visible, featuring a grill and seating area that invite outdoor relaxation.

Tiny home in Prineville

4.94 out of 5 average rating, 147 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.

Top guest favorite

A hot tub is illuminated by soft string lights against a wooden fence. The water surface shows gentle ripples, indicating bubbling jets, while a relaxing atmosphere is created by the warm glow surrounding the tub.

Cottage in Prineville

5 out of 5 average rating, 125 reviews

~Quail Run Cottage~

**Please read full description & look at all pictures to ensure it’s the right fit for your needs** This little gem is in the prime location. Located in the country but 5 minutes from the town of Prineville. It offers beautiful open views and nature all around. Take a load off & soak in the private hot tub & enjoy the scenery, it will not disappoint. Enjoy watching the quail run around the property along with other wildlife. **Please note- There is no washer/dryer/oven**

Guest favorite

A cozy sleeping area features a colorful quilt with patterned squares laid over a spacious bed. Two yellow pillows are positioned at the head of the bed. Natural light enters through a window beside the bed, illuminating horse-themed wall art and framed photos.

Tiny home in Mitchell

4.88 out of 5 average rating, 302 reviews

COPPINI’S Creekside Camp, Painted Hills

Coppini Creekside Camp is “glamping” at its best. Our cabin sits away from it all at the bend of Thompson Creek. Nesteled amongst beautiful juniper trees. A fire pit ,outdoor cooking station and a cooler with ice waiting for your beverages and perishables.Inside is a comfy queen bed and loft with a single mattress. Cabin has bathroom with camp shower and toilet. Tent available for guests that want more of the camping experience. Come, relax and have a super experience.