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Prineville vacation rentals

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Top-rated vacation rentals in Prineville

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

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Guest suite in Prineville

4.93 out of 5 average rating, 242 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).

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.

Home in Terrebonne

4.98 out of 5 average rating, 859 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!

Guesthouse in Powell Butte

4.89 out of 5 average rating, 102 reviews

Juniper Bunkhouse - newly renovated!

Enjoy either a relaxing or adventurous getaway located on a rustic ranch. Gorgeous views of Smith Rock, Grizzly Mountain and Cascade Mountains can be seen anywhere on the ranch as it is situated at the base of the Powell Butte. Feel free to take a short, easy hike to the edge of the property where there is a bistro table to sit at and admire the Sisters mountains as well as Mt. Jefferson and Mt. Washington. Walk route map provided at the time of stay. We are excited to share the views with you!

Home in Redmond

4.83 out of 5 average rating, 577 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.

Home in Prineville

4.97 out of 5 average rating, 113 reviews

Lakefront House with Amazing View Near Bend Oregon

Located in Central Oregon, 50 minutes from Bend, this newly renovated 4600 sq-ft lakefront home is a rare piece of paradise! This property has over 200 feet of year round private lakefront shoreline onto a 1,100 acre lake. Stunning lakefront views from almost every room in the house, luxurious décor, 5 bedrooms, and incredible options for both indoor and outdoor entertainment. This home was specifically designed and built for the ultimate year-round get-a-way vacation or executive retreat!

Loft in Prineville

4.85 out of 5 average rating, 214 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.

Home in Terrebonne

4.98 out of 5 average rating, 186 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.

Home in Redmond

4.95 out of 5 average rating, 294 reviews

Downtown Redmond Retreat

Welcome to our charming retreat nestled in the heart of Downtown Redmond! Situated amidst the tranquility of numerous parks in the Dry Canyon and the vibrant energy of downtown's breweries, restaurants, food carts, and shopping, convenience is at your fingertips. Just a quick 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend, our location offers easy access to nearby attractions. Step out of your front door, and adventure awaits in every direction...

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.

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.

Home in Prineville

4.98 out of 5 average rating, 106 reviews

Visit Rip’s Cabin in the Heart of Prineville

Experience the best of Central Oregon in this stunning 2017 downtown Prineville home! Ideal for families and traveling working professionals, this charming residence offers a convenient location within walking distance of restaurants and shopping. After a day of work or exploration, relax and marvel at breathtaking sunsets and stargazing opportunities. With easy access to Bend, Smith Rock, and the Painted Hills, this is the perfect base for both adventure and productivity.

Vacation rentals for every style

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Popular amenities for Prineville vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Prineville's top sights

Club Pioneer17 locals recommend

Bowman Museum16 locals recommend

Dillon's Grill15 locals recommend

Meadow Lakes Golf Course9 locals recommend

Crooked River Brewing8 locals recommend

Barney Prine's Steakhouse & Saloon8 locals recommend

Other great vacation rentals in Prineville

Condo in Prineville

5 out of 5 average rating, 28 reviews

Grizzly Getaway

Loft in Prineville

4.97 out of 5 average rating, 29 reviews

The Howdy Hideaway

Guesthouse in Prineville

5 out of 5 average rating, 10 reviews

Discovery Loop Landing

Home in Redmond

4.95 out of 5 average rating, 643 reviews

"Little Pine Cabin" attached to my home.

Home in Prineville

4.83 out of 5 average rating, 48 reviews

Beach Bungalow in Prineville, OR

Home in Terrebonne

4.96 out of 5 average rating, 431 reviews

Canyon House, Crooked River Ranch

Cottage in Prineville

4.94 out of 5 average rating, 51 reviews

Court St. Cottage | Downtown Prineville Getaway

Guest suite in Redmond

5 out of 5 average rating, 41 reviews

Cabin A

Quick stats about vacation rentals in Prineville

Total rentals
40 properties
Total number of reviews
2.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Prineville?
Yes! Work meets play with ease at over 10 vacation rentals in Prineville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Prineville?
Four-legged friends are welcome in Prineville. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Prineville?
Prineville has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Prineville have wifi?
Absolutely! We offer over 10 house rentals with wifi in Prineville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Prineville have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Prineville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Prineville?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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