Holiday rentals in Sisters

Cozy family cabin in Sisters, Central Oregon.

Relax with the family at this peaceful well appointed spacious cabin 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!

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!

Views! 1 Blk to Town,New+Spotless, 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

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.

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.

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.

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!

Awesome & affordable right downtown!

Welcome to your perfect home base in the heart of Sisters, Oregon! This inviting 1-bedroom, 1-bathroom getaway sits right in downtown Sisters, where Wild West-style wooden sidewalks, boutique shops, art galleries, and local eateries are just steps away. Whether you're here for a romantic getaway, a solo adventure, or a friends' trip, this comfortable space blends modern convenience with the relaxed mountain-town vibe that makes Sisters special.

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.

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.

Downtown Sisters - Ponderosa Building

This beautiful home in the heart of Sisters gives you easy access to all Sisters has to offer. Gourmet coffee and pastries are right down the street, and pizza is right next door. Relax on the beautiful covered deck or take advantage of nearby hiking, rock climbing, ski resorts, and the vibrant Sisters art scene.