Holiday houses in Sisters

The Quail Nest

Escape to this bright, modern studio in the charming town of Sisters, OR. Just a short walk to Peterson Ridge Trailhead, Downtown Sisters, and the Village Green, and a short drive to Hoodoo Ski Area and the surrounding National Forest trails, you’ll have easy access to everything this scenic town offers. Built in December 2024, this brand-new space provides a fresh, stylish retreat with everything you need for a relaxing getaway. Book your stay today and experience the best of Central Oregon!

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.

Sisters Peaceful Countryside Home

Located a quick 6 minutes to Sisters and only 15 minutes to Tumalo/Bend, this beautiful, serene ten acre property is perfect for your relaxing getaway. This hidden gem with spacious living areas and rooms, sleeps 6 guests comfortably, and we have provided 3 twin air mattresses for bigger parties. In the morning, enjoy your cup of coffee on our cozy outdoor living patio surrounded by a big beautiful yard and pond. If you're looking for a peaceful vacation, this is the place for you.

Downtown Pine Mountain Paradise

Classic Pine Meadow Paradise! 3 bedrooms and an additional ADU, this consists of one King bed, two Queen beds and two twin beds. You will love all of the natural light and french doors right off the living room. Fully equipped kitchen with Island. Master bedroom has mountain views, sandstone shower and soaking tub upstairs. There is also a private ADU over the garage guests are free to use. Enjoy sitting around on the wrap around porch with your favorite drink with family and friends.

Pine Grove Cabin, Sisters Oregon

Sisters, Oregon is the perfect vacation destination for those who love the great outdoors and Pine Grove Cabin is a comfortable and private base from which to explore. Close to a variety of outdoor activities, and a charming town center, it's the ideal place to relax and unwind. Whether you're seeking a romantic getaway, a family vacation, or a solo adventure, this vacation rental is the perfect for you. Book your dream vacation rental today and start planning your next adventure!

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.

A-Frame Cabin on 4.5 Acres - HOT TUB, Dog Friendly

This 2 bedroom Northwest themed A-Frame is the perfect destination for your couples retreat or small family vacation! It is situated on a super peaceful 4.5 acre lot and is only a 7 minute drive to Downtown Sisters. Our cabin sleeps 4 people comfortably in the 2 upstairs bedrooms, has 2 full bathrooms, a stocked kitchen, and a private back patio featuring our brand new hot tub. This is a dog friendly home so you are more than welcome to let your furry friend tag along!

Tollgate Retreat: Pool access. Trails & Near Town

Tucked just 5 minutes from downtown Sisters, this family-friendly retreat in Tollgate offers trails out the back door, a big patio, and access to a pool, sports courts, and more. Roam, explore the forest, or unwind with movies by the fire. Fully stocked kitchen, cozy bedrooms with individual heat controls, and space to truly relax. A peaceful basecamp for your next family adventure

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

Here’s a much better version: “Escape to my magical cottage, a peaceful sanctuary just steps from downtown. Nestled among tall Ponderosa pines with Whychus Creek flowing nearby, enjoy a lush private backyard perfect for stargazing from the hammock under dark night skies. Multiple decks, a covered gazebo with warm ambient lighting, and a private sauna await you.”

Smith Rock • King Beds • Steam Shower • No Pets

A wall of glass offers panoramic views of Smith Rock, blending indoor and outdoor spaces. This modern home on the rimrock is flooded with sunlight, featuring king beds and a luxurious steam shower. Enjoy a peaceful setting with probable wildlife sightings and a cliff-edge deck for relaxing. Smith Rock State Park is less than 5 minutes away and always in view.

Renovated Sisters Condo; perfect getaway!

Completely renovated in 2019, this 2 bedroom/2 bath condo is a delightful get-away! Walking distance to downtown Sisters, nearby movie theater, spa and restaurants. Perfect location for relaxing vacation or a get away full of day trips to surrounding sites! Hot tub and recreational room access year around, heated pool is open Memorial Day through Labor Day!

Private Peaceful Cabin in Sisters!

Upon your arrival in Tollgate, a wonderful community only 1.5 miles out of Sisters, you will feel the stresses of your everyday life magically drop away as you are surrounded by the serenity and beauty of a Ponderosa Pine forest within the quiet ambiance of Tollgate.