Holiday houses in Sisters

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!

Cozy Cabin near Sisters

Escape to this serene mountain-view cabin, perfect for a peaceful getaway. Enjoy breathtaking vistas, cozy up by the fire, and bring your furry friends—dogs are welcome! With a fully equipped kitchen and modern comforts, it’s your ideal retreat for relaxation and adventure. Wander the grounds and relax by the private pond and waterfall feature. A true back-to-nature escape with just the right touch of comfort. Located 5 miles outside of Sister’s and 1 mile from the famous Sisters rodeo grounds.

Views! 1Blk to Town, Clean+Charming,pets ok-Middle

Prime Sister's location, Safe upscale neighborhood! Newly built condo offers EVERYTHING you expect without sacrificing a thing! Only 1 block to downtown restaurants/shopping. Leave your car at the unit and walk! Fully stocked Kitchen, comfy king size bed in master, queen size sofa / sleeper in living room! Relax on sofa or the new recliner, excellent wi-if, internet, cable tv, Netflix. Washer/dryer to use too! Pet friendly, under 40 lbs, $35.00 pet fee per pet. This unit is also ADA co

Cozy Remodeled Log Cabin - HOT TUB - Large Deck!

Enjoy your own private saltwater hot tub under the tall pines at this updated 3-bedroom cabin in Sisters, OR. Set on a quiet 1-acre lot in the Crossroads neighborhood, it’s just 5 minutes from the shops and restaurants of downtown Sisters. Inside you’ll find vaulted ceilings, beautiful wood beams, a modern kitchen, updated bathrooms, and a full laundry room. Relax on the large back deck, sip coffee on the covered front porch, and make lasting memories in this perfect Central Oregon getaway.

Serene family cabin in Sisters, Oregon.

Peaceful, well appointed spacious cabin in a Dark Sky community that embodies the spirit of central Oregon. The cabin is located 3 miles from Downtown Sisters, 20 minutes to Hoodoo & 10 minutes to Black Butte Ranch. We've geared the spaces towards fun and relaxation. Well curated amenities will help your family enjoy all that the Sisters area has to offer. From an easy to use propane fireplace to a fenced backyard for your pup, fully stocked kitchen, comfy beds and kid friendly amenities!

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.

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.

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.

Luxe A-Frame Retreat in Sisters

Welcome to the best house in the best part of Central Oregon. Located just minutes from downtown Sisters, this fully-renovated 1966 A-frame is a year-round basecamp with stunning mountain views. Throw a bbq after a day hiking in the Three Sisters Wilderness. Unwind in the hot tub after after powder laps on the mountain. Or just cozy up and enjoy the view from in front of the fireplace and never leave. Whatever your taste for adventure or relaxation, this cabin is outfitted.

Walk to Town Family Meeting Place AIRBNBOB

Home built in 2017 with AirBnb in mind. Private entrance. Smart lock access to upstairs flat. Master bedroom with king bed. Balcony bedroom with amazing queen electric bed (New). Trundle couch with two single beds. Electric cooking area. Mini fridge. Balcony view of snowcapped mountains. High speed WIFI. Wide Screen TV. Apple TV access to Netflix, Youtube, Amazon Prime, etc. New Bidet installed in April 2019.

Downtown Sisters- *New* 1 Bedroom Condo

Enjoy staying in the heart of downtown Sisters. Just two blocks from the Main Street, this brand new unit will have everything you need for your getaway. This bright and open condo is located on the second floor of a two story building. Featuring brand new furniture, queen mattress, appliances and a fully equipped kitchen. Explore all the wonderful surroundings in Sisters and come home and relax in this great space!

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

“Escape to a special place I call my cottage, a peaceful sanctuary just steps from downtown. Nestled among tall Ponderosa pines with Whychus Creek flowing nearby, for a quick cold plunge. Enjoy a lush private backyard perfect for stargazing from the hammock under the night sky. Multiple decks, a covered gazebo with warm ambient lighting, and a private sauna await you.”