Holiday rentals in Jefferson County

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Top-rated holiday rentals in Jefferson County

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

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Top guest favourite

Home in Terrebonne

4.98 out of 5 average rating, 886 reviews

Cozy Three Story Lookout Tower

BrookeRating, 5 stars2 weeks ago

What a special place!!! We loved our stay here. We had beautiful clear days that allowed us to see all of the surrounding mountains. The sunsets were STUNNING! The lookout tower house was so unique and we loved all of the windows for those 360 views on the top floor. We will definitely be back.

Top guest favourite

Home in Terrebonne

4.98 out of 5 average rating, 271 reviews

Pointe of Blessing with hot tub and canyon views

DouglasRating, 5 starstoday

We stayed here for 4 nights while exploring the area. The location is beautiful, and the house is very clean and comfortable. We enjoyed soaking in the hot tub as well as lovely sunrises, sunsets and so so many stars. Angelle's communication was excellent from start to finish. Check-in was a breeze. We highly recommend Pointe of Blessing.

Guest favourite

Guest house in Prineville

4.82 out of 5 average rating, 11 reviews

Ochoco guest cabin!

BrianRating, 5 stars8 months ago

5 stars!! Jacqueline and Jason are very accommodating, they made us feel comfortable and welcome! We loved the beautiful location, out in the country but close enough to town (15 minutes) to keep things easy and simple. The cabin/apartment was very comfortable and plenty spacious enough for the 4 of us. The bathrooms, bedrooms, linens, furniture, countertops and floors were all very clean and the place was well organized. We hope to stay here again next time we're in the area! :)

Guest favourite

Cabin in Camp Sherman

5 out of 5 average rating, 13 reviews

Aspen Cabin at House on Metolius

Tanya C.Rating, 5 stars7 months ago

This cabin was even better than the pics and description. It even had heated bathroom floors. And the setting was absolutely stunning. My husband fished every day and I had plenty of places to walk and explore. And the town of Sisters is adorable with lots of cute shops and places to eat. We’ll definitely be back.

Guest favourite

Cabin in Culver

4.91 out of 5 average rating, 158 reviews

Cabin on The Rim

TaylorRating, 5 stars1 week ago

Just like other reviews have said, pictures do not do this beautiful space justice. The bed was very comfortable and the wood stove was excellent. Some extra amenities included 40L of water, a very nice cooler, plenty of firewood, a towel for the outdoor shower, and a clean and well stocked porta-potty. The cabin also came with some grilling utensils, two pans, a kettle, and a french press. We wished we had brought more of a camp kitchen (plates, bowls, silverware), but otherwise this space was perfect. Bring binoculars if you want some excellent bird watching! We can't wait to visit again.

Top guest favourite

Tiny home in Prineville

4.94 out of 5 average rating, 140 reviews

Tiny Pine house in the Ochocos at Wine Down Ranch

MarvinRating, 5 stars1 month ago

Had trouble getting through the draft from rain/melted snow because the tesla was a but too low, but they allow me to use their utility terrain vehicles (UTVs) to transfer items from car to our tiny home rental, and they allowed me to use for the couple of days I was there. I thought this was very sweet. Thank you Mary and roy.

Top guest favourite

Home in Terrebonne

4.96 out of 5 average rating, 452 reviews

Canyon House, Crooked River Ranch

JadeRating, 5 stars1 week ago

Beautiful place to stay! If you’re looking for a quiet and private getaway- this place would be a perfect spot. This is the second time my husband and I came, first time was on our honeymoon and we loved it so much we had to come back! Beautiful views to sit in the hot tub and relax. Really close to hiking trails and smith rock. Jeff is also very responsive, very friendly. I will always recommend this place!

Guest favourite

Cabin in Crooked River Ranch

4.94 out of 5 average rating, 110 reviews

Classic Cozy Cabin with Awe-inspiring Views

AmieRating, 5 stars2 months ago

This cabin was exactly what we were looking for as we were visiting family in the area for a few days. It was quiet and a beautiful setting. All of the amenities of home. Host was extremely responsive with our questions. We will definitely be back in that area and looking to stay here again.

Top guest favourite

Tent in Terrebonne

5 out of 5 average rating, 9 reviews

Volcano Outlook

KyleeRating, 5 stars1 month ago

Perfect compromise between camping (fiancé’s preference) and hotel (my preference)! Lol. GORGEOUS views, peaceful, private location, dog friendly, communicative and friendly hosts... It was pretty cold and windy when we were there, but even then, it was a decent experience for what it was! Looking forward to coming back and enjoying it again in warmer weather. 😉

Holiday rentals for every style

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Houses

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Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Jefferson County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Jefferson County

Guest favourite

Cabin in Crooked River Ranch

4.87 out of 5 average rating, 79 reviews

Classic Cozy Cabin with Awe-inspiring Views

MilaRating, 5 stars8 months ago

Great place to spend one night. It was quiet and peaceful, bed was comfortable and we had everything we needed. Beautiful surroundings, green lawn, outside dining area. Highly recommended place for one or two people.

Superhost

Cabin in Camp Sherman

5 out of 5 average rating, 27 reviews

Metolius River Resort Cabin 12 Luxurious cabin on

AliciaRating, 5 stars11 months ago

Cabin is beautiful and very clean. Great location near the river.

Hotel room in Madras

4.67 out of 5 average rating, 3 reviews

Budget Inn Queen Bed

CaitlynnRating, 5 stars9 months ago

Easy, responsive, and in a central area.

Top guest favourite

Ranch in Prineville

4.93 out of 5 average rating, 390 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

MariaRating, 5 stars1 month ago

This totally matched what I was looking for in terms of nature, peace, and comfort. I enjoyed the beautiful clouds from the sunrise and sunset off the hilltops. The animals surrounding the land were super endearing as we were able to pet the horses during our stay. This was a great getaway from technology and the hustle and bustle of the city. Mary and Roy were very responsive and super kind.

Superhost

Private room in Terrebonne

4.86 out of 5 average rating, 49 reviews

Room with 2 full beds by Golf course and Trail

AnthoniaRating, 5 stars17 months ago

Very friendly staff. The location is beautiful with lots of fun things to do. Hiking, fishing and golf. This is probably the cleanest place we have ever stayed in. Nothing bad to say about Smith Rock Resort.

Top guest favourite

Private room in Metolius

4.97 out of 5 average rating, 65 reviews

Private bedroom and bath with private entry.

JamieRating, 5 stars9 months ago

Tryna was very friendly made the stay feel like home

Top guest favourite

Private room in Madras

5 out of 5 average rating, 10 reviews

Perfect for traveling nurse!

SiennaRating, 5 stars5 months ago

Katie and Jay are wonderful hosts and made me feel right at home. It was an added bonus that they also have the sweetest pets to keep you company. This was the perfect place to stay for a month long medical school rotation with the hospital just down the road. I highly recommend and would stay here again.

Superhost