Holiday rentals in Prineville

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Top-rated holiday rentals in Prineville

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

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Guest favourite

Guest suite in Prineville

4.93 out of 5 average rating, 219 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).

17–24 Oct

$158 SGD per night

Guest favourite

Flat 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.

11–18 Oct

$192 SGD per night

Guest favourite

Farm stay in Prineville

4.93 out of 5 average rating, 368 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.

31 May – 7 Jun

$141 SGD per night

Guest favourite

Cottage in Terrebonne

4.91 out of 5 average rating, 258 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!

18–25 Aug

$197 SGD per night

Guest favourite

Home in Terrebonne

4.98 out of 5 average rating, 163 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.

2–9 Sep

$258 SGD per night

Guest favourite

Home in Redmond

4.82 out of 5 average rating, 518 reviews

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

18–25 Jan

$130 SGD per night

Guest favourite

Home in Terrebonne

4.99 out of 5 average rating, 168 reviews

Smith Rock Gardens

You'll enjoy the main house with the best views of Smith Rock and the Cascade mountains. Smith Rock State Park is literally across the street. A great location for outdoor activities at the park or in the region. Hike, climb, bike, walk or jog around the park. Sip tea inside and watch the animals. Perfect for artist and photographers. Relax on the deck or enjoy a sunset BBQ with gorgeous views. Owners live in adjoining unit. Separate entrance. Instagram: @smithrockgardens DCCA Tax# 1784

$267 SGD per night

Guest favourite

Tiny home in Redmond

4.99 out of 5 average rating, 185 reviews

Tranquil Views, Country Cozy, Close to Smith Rock

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 :)

6–13 Dec

$182 SGD per night

Guest favourite

Flat in Mitchell

4.94 out of 5 average rating, 514 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.

19–26 Feb

$182 SGD per night

Guest favourite

Home in Terrebonne

4.99 out of 5 average rating, 117 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.

31 Aug – 7 Sep

$735 SGD per night

Guest favourite

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 .

21–28 Feb

$122 SGD per night

Guest favourite

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.

25 Nov – 2 Dec

$197 SGD per night