Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

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

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Top guest favorite

A comfortable living area features a spacious blue sofa adorned with cushions in various shades of blue. A brown recliner is positioned nearby, with a wooden side table that holds a lamp. A wall with sunset artwork is prominent, complemented by a window allowing natural light.

Guesthouse in Culver

5 out of 5 average rating, 18 reviews

NEW! Modern, Close to Nature | Working Farm Stay

COPPER CORRAL PROPERTIES is proud to welcome you to Sunset&Sage! Prepare to slow down and listen to the land when you check into Sunset & Sage. This guest house has endured for over 80 years, growing from a one room cabin to a cute and modern get away in the middle of quiet farm fields. The Crooked River National Grasslands and Haystack Reservoir are both within sight of your front door, and you can watch the sun set over Mt Jefferson in the evening. Smith Rock State Park is just a quick dri

Top 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, 912 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

An open living space is visible, featuring a comfortable black couch with a plaid throw. A modern kitchen area with stainless steel appliances is seen, along with a dining table in the background. Warm wood flooring enhances the inviting ambiance.

Guesthouse in Terrebonne

4.86 out of 5 average rating, 257 reviews

Near SmithRock pets ok low cost private cold ac

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Top guest favorite

A cozy living area is presented with a dark sofa adorned with colorful cushions. A guitar and artwork are displayed on the walls. Natural light filters through a large window, complemented by houseplants and warm lighting from a standing lamp.

Cabin in Prineville

4.98 out of 5 average rating, 61 reviews

Cabin in the Ochocos

Our cabin/guest house is located on 32 acre forested property next to the main house and is a perfect base camp for hikers, bikers, hunters, dark sky and winter sport enthusiasts. It overlooks Upper McKay Valley, is one mile from the north entrance of Ochoco National Forest and 10 minutes north of downtown Prineville. Ideal for 2 but can accommodate 4 people to share the amenities of a small scale fully equipped home. Amazing views with farm animals to round out the country living experience.

Superhost

The cozy cottage exterior is highlighted by warm light emanating from the windows at dusk. Two comfortable chairs are positioned on the wooden porch, inviting relaxation. A small fire pit is visible in the foreground, with a shed seen in the background.

Cabin in Culver

4.85 out of 5 average rating, 26 reviews

Garden Cottage

This peaceful garden oasis is the perfect launching point for your next Central Oregon adventure. The cottage is located on a working ranch, just 10 minutes from either Smith Rock State Park or Lake Billy Chinook, and adjacent to the Crooked River National Grassland. After hiking the ranch’s trail into the Crooked River Gorge, or adventuring off site, enjoy the views of the buttes and horses grazing in the pastures as you unwind on the front porch. There is a porta potty and outdoor solar sho

Top guest favorite

The exterior of the cabin is surrounded by lush grass and tall trees, featuring a combination of natural wood doors. A large window allows light into the interior, while two chairs offer a place to relax outdoors.

Cabin in Camp Sherman

4.89 out of 5 average rating, 155 reviews

Camp Sherman Oregon Private Cabin Mt Jefferson

Small Cabin located near Lake Creek Lodge and Fire Station/Community Hall on the main road into Camp Sherman. This cabin is located on 1 acre property with grass and park area that includes, campfire area, horseshoe pit and pond (no swimming). Bike & hike trail adjacent to the store /river Perfect getaway, great condition with granite island and counter tops, knotty alder cabinets. Over 300 DVD collection. Wi-Fi Starlink, if remote working is necessary. GUESTS MUST CLEAN THE CABIN!!!

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

4.98 out of 5 average rating, 293 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.

Top guest favorite

A cozy living room features a comfortable sofa, an accent chair, and a coffee table. A 60" smart TV is positioned across from the seating, while a large window allows natural light to fill the space. Decor includes a mirror and plants, enhancing the inviting atmosphere.

Home in Madras

4.98 out of 5 average rating, 56 reviews

Madras Oak House

This cozy 2-bedroom, 2-bathroom house is the perfect retreat for your stay in the heart of Madras. Full access to the entire 926 sqft house. Enjoy unopposed mountain views and short driving distances to downtown, restaurants, Willow Canyon trail, Sahalee Park, Deschutes River, Cove Palisades and Smith Rock State Parks. **Due to severe allergies, no smoking on premises and no pets are allowed. If you bring a pet, you will be asked to leave and will be charged $200 for extra cleaning.**

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

4.91 out of 5 average rating, 193 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, 144 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

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

Home in Terrebonne

4.96 out of 5 average rating, 464 reviews

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

Guest favorite

A log cabin with a large front deck extends to the outdoors, surrounded by natural landscaping. The structure features a sloped roof and large windows that invite ample sunlight. Tall trees and rocky terrain complement the tranquil setting.

Cabin in Terrebonne

4.98 out of 5 average rating, 308 reviews

Steelhead Falls Log Cabin

Enjoy a restful time in our waterfront log cabin along the Deschutes River. Location is perfect for watching wildlife, fly fishing, quiet relaxation, and has easy access to hiking and rock climbing at Smith Rock and Lake Billy Chinook. Steelhead Falls is a a short hike away. Bend and Sisters are near. Unfortunately, we cannot accommodate even small weddings. We recommend access to AWD vehicle with either chains or snow tires in winter. Dog friendly- sorry, no cats.