House vacation rentals in Jefferson County

4.98 out of 5 average rating, 886 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!

4.98 out of 5 average rating, 270 reviews

Pointe of Blessing with hot tub and canyon views

We hope you will enjoy our Pointe of Blessing. We feel our canyon perch is a gift from God-just 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. Prepare to relax unwind and enjoy spectacular sunrises and moonrises.

4.98 out of 5 average rating, 49 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.**

Superhost

5 out of 5 average rating, 3 reviews

Two Updated Units, Entire Duplex, 4BR, Sleeps 12

Experience the comfort of our recently renovated duplex, with two separate living quarters. Each unit has 2 bedrooms, 1 bathroom, a kitchen, and a living room, totaling 4 bedrooms and 2 bathrooms. Ideal for two families, the units are connected by an outside door with a covered walkway. Centrally located in Madras, Oregon, our home offers a cozy haven for a delightful stay. Enjoy nearby activities like hiking, fishing, and boating at Lake Billy Chinook or exploring Smith Rock State Park.

Guest favorite

5 out of 5 average rating, 6 reviews

Ride, rest, repeat. Mountains Galore

Kick back and relax in this calm, stylish space. Settled in the middle of Mt.Hood and Mt.Bachelor you'll be an hour from the largest mountain resorts in Oregon. Plus, just a short drive to all of the restaurants and activities in Redmond, Bend, and Sunriver. Spend the day riding, then come back to the country to relax and unwind on our back deck with picturesque sunsets, sprawling mountain views, and an expansive night sky. Then do it all again the next day. Play hard, recover, repeat!

4.96 out of 5 average rating, 452 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.

4.51 out of 5 average rating, 43 reviews

Experience Serenity w/ Mountain Views & Home Gym

Escape to a serene and stunning mountain view retreat in the high desert. This ranch home offers an unparalleled connection with nature, set on a beautiful farm and surrounded by breathtaking views of the Cascade Mountains. Perfectly located just 5 minutes from downtown Madras, and within easy reach of other exciting central Oregon towns, this retreat offers the perfect blend of peaceful seclusion and convenient access to local attractions.

4.93 out of 5 average rating, 28 reviews

Home in Culver

L&T Chinook Properties

Relax in this quiet little hideaway. 2 buildings included. Spacious 2 bedroom house located 5 min from Cove Palisades State Park. The other building is an outdoor living space (no ac) which provides a kitchen, bathroom, grill, outdoor patio , fire pit, and ton of space with extra sleeping. It’s a quiet little community on the edge of the state park that provides Mountain View’s for days.

Guest favorite

4.93 out of 5 average rating, 73 reviews

All Mountain View’s Retreat

Beautiful A frame style home with lots of natural light. Views of Mt Jefferson and the Sisters Mountain Range. Park like setting with privacy. Large deck with BBQ, propane fire pit, patio furniture and picnic table. Large fenced yard and plenty of parking. Near Smith Rock, Bend, Lake Billy Chinook, Maragas Winery, Alpaca petting farm and many other tourist attractions.

Home in Warm Springs

4.85 out of 5 average rating, 156 reviews

Private Oasis on Warm Springs Reservation

Very private house on the Warm Springs Indian Reservation. Located ten minutes from the Indian Head Casino. We are nestled amid sagebrush hills, juniper trees, and no city lights to diminish the beautiful stars at night. This is the perfect, quiet getaway to explore Central Oregon and the high desert countryside or enjoy the casino and come back to a quiet retreat.

Guest favorite

4.95 out of 5 average rating, 22 reviews

Renovated 2BR with Private Back Yard - Sleeps 6

Experience the comfort of our recently renovated 2-bedroom, 1-bath retreat located in the heart of Madras, Oregon. Perfect for those seeking a modest yet delightful stay, our home provides a cozy haven. For added convenience, St. Charles Medical Center is just a 2-minute drive for anyone traveling to work at the hospital.