Holiday rentals in Deschutes County

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Top-rated holiday rentals in Deschutes County

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Top guest favourite
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, 263 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).

Top guest favourite
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, 527 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 favourite
A cozy living area is featured with wooden beams and warm finishes. A light-colored sofa is positioned near a small kitchenette with a kettle and dishes. A ladder leads to an upper sleeping area, while a decorative rug adds softness to the floor.
Guest suite in La Pine
4.95 out of 5 average rating, 218 reviews

ForestView Guest Suite + HotTub and Infrared Sauna

Private guest suite within our newly 2023-built home. Separate backyard area with Cabin In Deschutes Spa where the modern amenities meet the beauty of nature. Rest as calm as the doe and the fawns outside while staying seamlessly connected with high-speed 300 Mbps Wi-Fi. Savor the luxury of a hot tub and infrared sauna while watching as the squirrels teach their young to leap trees. This is life — a campfire to relax by, a sunset to inspire — in a home, guarded by pines framing the Milky Way.

Guest favourite
A living area features a dark leather couch and a patterned armchair, centered around a wooden coffee table. Natural light filters through the window, illuminating the warm tones of the room. A landscape painting hangs on the wall, enhancing the inviting ambiance.
Home in Redmond
4.84 out of 5 average rating, 652 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.

Top guest favourite
A bright great room features large windows that invite natural light and views of the surrounding greenery. A gas fireplace is situated beneath a framed artwork. Comfortable seating includes a sectional sofa and armchairs, complemented by a coffee table adorned with decorative plants.
Townhouse in Redmond
4.91 out of 5 average rating, 137 reviews

Quiet Eagle Crest Townhouse w/ Access to Amenities

Enjoy all that Central OR has to offer in this quiet, end-unit townhouse. Located in Eagle Crest Resort, a 1700-acre resort with one spa, three sports centers, five pools, and three full year-round golf courses, it is the ideal location to enjoy Central OR. This 1400sq ft single-level townhome features a great room with soaring ceilings, walls of windows, a fully stocked kitchen, and plenty of gathering spaces. Perfect for a romantic getaway, fun family weekend, or adventure-filled vacation.

Top guest favourite
A bright living space is highlighted by large windows allowing natural light to fill the room. Comfortable seating options, including a blue sofa and various chairs, are arranged around a rustic coffee table. A television stands in the corner, enhancing the casual atmosphere.
Home in Terrebonne
4.98 out of 5 average rating, 258 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

Top guest favourite
A spacious outdoor deck is furnished with two Adirondack chairs facing a circular fire pit. A panoramic view of distant mountains and valleys is framed by a railing, showcasing the landscape under clear blue skies.
Flat in Redmond
4.97 out of 5 average rating, 537 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 daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

Top guest favourite
The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.
Home in Bend
5 out of 5 average rating, 282 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

Top guest favourite
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, 297 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.

Top guest favourite
A small balcony is visible, featuring two woven chairs and a round blue table. Panoramic views of the surrounding landscape and distant trees can be seen, with clouds casting soft shadows over the scene and sunlight filtering through the open space.
Flat in Redmond
4.98 out of 5 average rating, 202 reviews

Mountain View Suite near Smith Rock - Fast Wi-Fi

FAST INTERNET. Quiet rural location a few miles from town on rimrock over a small canyon. Enjoy a wide view of the Cascades from a roomy studio apartment that is comfy and uncluttered. Features a big bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. Crib on request. Extra fee: 1) per pet 2) roll-away bed. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 min

Top guest favourite
The RV interior features a spacious living area with a large sectional sofa and a central kitchen island. Modern appliances, including a stovetop and refrigerator, are visible, along with ample cabinetry. Windows provide natural light, framed by simple curtains, and a soft area rug adds comfort.
Campervan/Motorhome in Bend
4.97 out of 5 average rating, 175 reviews

Glamping! Quad Slide RV on a Tumalo Hobby Farm

Welcome to the Tumalo hobby farm! Here you will have your own 42ft 2019 Forest River RV, located on our lovely Tumalo property. Nestled in the midst of goats and chickens, this will be a perfect landing for work or play. Enjoy the mountain views and bright stars after your day out adventuring around Central Oregon. Within close driving distance to Bend, Sisters, Redmond, Mt Bachelor and Hoodoo. This RV is fully hooked up with power, water, heat, A/C, internet, and is ready for you.

Guest favourite
Two Adirondack chairs are positioned on a patio, facing a stunning sunset over distant mountains. A small table is located between the chairs, accompanied by a flower pot. The sky is painted with hues of pink, orange, and purple, creating a serene atmosphere.
Guest suite in Powell Butte
4.96 out of 5 average rating, 234 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!

Popular amenities for Deschutes County holiday rentals

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