Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

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Top guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 898 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!

Top guest favorite

Two dark-colored farm animals are seen interacting in an open grass area. Their soft coats and large ears are prominent features. The background is blurred, directing focus to the animals, while patches of sunlight create a gentle pattern on the ground.

Cabin in Prineville

4.98 out of 5 average rating, 54 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.

Top guest favorite

An outdoor lounge deck features orange-painted walls, furnished with two chairs and a table. The setting is surrounded by low greenery and scattered trees, providing a rustic atmosphere. A canoe and additional outdoor decor can be seen in the background.

Tent in Terrebonne

5 out of 5 average rating, 14 reviews

Volcano Outlook

Large, 16X20 glamping tent on an insulated platform, above the Deschutes River. Walk to the Steel Head Falls in 20 minutes. Our tent has 1 queen size bed, and also a futon, that can be made into a bed. The tent has electrical and water inside the tent. Enjoy hiking, biking, fishing, golfing or kayaking in Central Oregon. Local access or day trips. Beautiful views of the Cascade Mountains. Matching platform for relaxing and cooking outside, with hot shower located behind. Outhouse too.

Guest favorite

The cabin's entrance is framed by natural wood siding and features a welcoming wooden door with window panes. A decorative sign and a plant in a terracotta pot add to the exterior charm. A pathway leads to the door, with a green lawn visible beyond.

Cabin in Camp Sherman

4.89 out of 5 average rating, 151 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!!!

Guest favorite

A winding paved road leads toward a rustic log entrance, framed by natural rock formations and tall pine trees. The open landscape showcases a serene environment, inviting exploration of the surrounding area.

Guesthouse in Prineville

4.83 out of 5 average rating, 12 reviews

Ochoco guest cabin!

Take it easy at this unique and tranquil getaway. Located 1 mile from the Ochoco National Forest, this superior craftsmanship cabin is sure to accommodate to all your vacation needs from hunting to exploring. Located on the Crooked River, Prineville is a combination of fascinating history and scenic pristine outdoors with a variety of recreational opportunities including rockhounding, fishing, hiking, boating and much more. Please reach out with any request. Meal options also available.

Top guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 283 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 well-lit workspace features a sleek white desk paired with a blue upholstered chair. A small potted plant adds a touch of greenery, and a stylish lamp provides illumination. Natural light streams in through a nearby window, enhancing the serene atmosphere.

Home in Madras

4.98 out of 5 average rating, 52 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

The cabin is perched on a rocky hillside, surrounded by lush green foliage and trees. A panoramic view of the valley and distant hills is visible under a clear blue sky, providing a serene and natural backdrop for the getaway.

Cabin in Culver

4.91 out of 5 average rating, 174 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

The interior showcases rustic blue pine walls with a well-equipped kitchen area featuring a wooden countertop and modern appliances. A small propane stove is visible beside the staircase, leading to an upper loft. Natural light pours in through multiple windows, enhancing the warm ambiance.

Tiny home in Prineville

4.94 out of 5 average rating, 143 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.

Superhost

A wooden table is set in front of a stone fireplace, where flames can be seen glowing warmly. A plate of pepperoni pizza garnished with artichokes and red peppers is displayed alongside a glass of beer and a bottle of red wine.

Cabin in Camp Sherman

4.8 out of 5 average rating, 15 reviews

Creekside Studio Cabin at Lake Creek Lodge

Cabin 7 at Lake Creek Lodge is the coziest of them all, with a fireplace literally at the foot of your queen bed. Located just downstream from the main Lodge in a wooded area that is perfect for watching the wildlife, this cabin has a kitchenette and private bath with everything you'll need for a comfy stay. Bring your pooch to hike the Metolius Basin trails, fly fish our private pond, swim in our seasonal pool and enjoy fun evenings in Lake Creek Lodge's restaurant and bar.

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, 456 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.

Top guest favorite

The exterior of a charming A-frame cabin is shown, featuring a spacious deck with wooden railings and steps. The cabin is painted in soft green, with decorative features on the façade and large windows that allow natural light to fill the interior.

Cabin in Culver

4.98 out of 5 average rating, 43 reviews

Cozy A- Frame at Lake Billy Chinook in Culver Or.

Relax and come play at our cute A frame cabin only 3 miles from one of the many boat docks at Lake Billy Chinook(only a 5 minute drive). This 2 bed/2 bath A frame cabin has been meticulously set up to provide guests a comfortable place to stay without sacrificing amenities. This cute A frame offers adventures, relaxation, and endless fun. With the lake, hiking trails, and outdoor adventures close by, you will not have to look far to keep busy during your stay.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

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Stylish accommodations and amenities

Popular amenities for Jefferson County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Jefferson County

A bright corner in the loft features a comfortable chair alongside a modern desk and office chair. Natural light filters through a large window framed by unique shutters, illuminating the space and offering views of the surrounding landscape. A colorful area rug adds warmth to the hardwood floor.

Private room in Terrebonne

5 out of 5 average rating, 3 reviews

The Loft at The Spot.

LaurieRating, 5 stars1 week ago

Michelle and Evan were amazing hosts! Quick to answer all questions and made me feel so welcome in their home. I would stay here again in a heart beat.

Guest favorite

Campsite in Camp Sherman

4.91 out of 5 average rating, 11 reviews

Lake Creek Campsite - The Property at Camp Sherman

KerryRating, 5 stars3 days ago

This property is gorgeous! Private, quiet, peaceful… just right for a getaway in the beautiful PNW. We pitched tents, enjoyed a creek side fire, and felt right at home. The amenities were just as described, and we will certainly be back. Thank you! 🙏🏻

A reception area features a wooden front desk with a marble countertop. Natural light enters through large windows, illuminating the space. A door leads to the guest rooms, and a wall-mounted display stand is visible near the entrance.

Hotel room in Madras

4.67 out of 5 average rating, 3 reviews

Budget Inn Queen Bed

CaitlynnRating, 5 stars11 months ago

Easy, responsive, and in a central area.

Top guest favorite

Home in Madras

4.98 out of 5 average rating, 43 reviews

Newly Remodeled 2BR Retreat with Private Backyard!

RaymondRating, 5 stars1 week ago

We had a wonderful stay at the Madras home! The space was exceptionally clean, thoughtfully designed, and very comfortable for our family. One of the highlights was the excellent A/C units—such a relief in the summer heat, especially after spending time outdoors. The home provided the perfect balance: we were able to enjoy the beautiful surroundings and local activities, while also having a quiet, restful space to recharge during an in-state holiday. Everything was just as described, and we’d happily stay here again. Highly recommend!

Guest favorite

A row of iron hooks in a rustic design is mounted on a textured wall. The hooks, shaped like horseshoes, are arranged alongside a decorative star, providing a practical and charming feature. A mirror reflects the hooks, adding depth to the scene.

Ranch in Prineville

4.93 out of 5 average rating, 393 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

AngelaRating, 5 stars1 week ago

Mary’s bunkhouse was perfect in every way. This property is an amazing slice of heaven away from the hustle & bustle of everyday life. Beautiful place to unwind & relax. I can’t say enough good things about Wine Down Ranch & Mary is the best, will definitely by back soon!

Superhost

A scenic overlook captures a rugged canyon landscape with steep rock cliffs and a winding river below. Various pine trees dot the dry terrain, while a wooden railing provides safety at the viewpoint. The sky features scattered clouds and bright blue patches.

Private room in Terrebonne

4.86 out of 5 average rating, 50 reviews

Room with 2 full beds by Golf course and Trail

KtRating, 5 stars1 month ago

This place is gorgeous! Right on a beautiful gorge & river, with bunnies running about! Room was clean with all the necessities, and parking right by the door. It's about a 20 min drive from Smith Rock State Park.

Top guest favorite

A private bathroom is shown through an open door. Vintage wallpaper decorates the walls, complemented by a small framed mirror. A toilet is positioned beside a window with a sheer curtain. A towel and toilet paper holder are also visible, adding to the bathroom's functionality.

Private room in Metolius

4.97 out of 5 average rating, 69 reviews

Private bedroom and bath with private entry.

HaiRating, 5 stars3 weeks ago

We stayed one night over Memorial Day weekend to visit Culver (this place is very close to the Cove Palisades) before heading to the Painted Hills. Tryna is a welcoming host. The room is clean and opens to a comfortable sitting area on the patio. We woke up to delicious coffee! Perfect stay for sightseeing the surrounding natural wonders of Central Oregon. We definitely recommend this place and would stay here again.

Top guest favorite