Family-friendly holiday rentals in Sisters

Serene family cabin in Sisters, 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!

Indoor spaces · Kitchen · Barbecue

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!

Indoor spaces · Kitchen · Parking

Cozy Mountain Escape: Amazing Views! Hot tub!

Relax in this calm, stylish newer home! The unobstructed mountain views are Jaw-dropping!! Walking distance to all that this amazing town has to offer. Enjoy the mountains and wildlife from the upper and lower decks after a day of exploring. Located in the desirable Pine Meadow Village neighborhood. Includes access to clubhouse, with a seasonal pool and a hot tub. You will take part of the mountain escape experience with you, wherever you go, and the memories you create will last a lifetime!

Family · Kitchen · Heating

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.

Indoor spaces · Family · Access

Pet + kid friendly w/ private hot tub!

Relax with the whole family at this peaceful cabin in Sisters! Take a short drive into downtown Sisters or ride bikes into town via neighborhood trails to do some shopping or explore the nearby lakes, rivers and mountains. Or stay in! Enjoy happy hour on the roof top deck, unwind in the steamy hot tub, cook dinner in the fully equipped kitchen, or have a BBQ on the outdoor patio! This is the perfect place to experience all Sisters has to offer! Just the getaway you've been waiting for!

Indoor spaces · Family · Breakfast

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.

Kitchen · Family · Bathroom

Apartment in Sisters, OR. USA

A contemporary 2 bedroom apartment in a quiet neighborhood just 4 blocks from Sisters main street. Minutes from music venues, festival locations, trails, and popular biking routes. Sisters has art, music, movie theater, good coffee, beer, restaurants, and boutique shopping. Village Green is close by. Superb biking, hiking, skiing, fly fishing, and outdoor opportunities abound year round. The apartment is perfect for couples, solo adventurers, business travelers, and families.

Kitchen · Indoor spaces · Accuracy

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!

Family · Indoor spaces · Location

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.

Indoor spaces · Family · Parks

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.”

Kitchen · Indoor spaces · Backyard

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.

Kitchen · Family · Wi-Fi

*Brand New* Modern 1 Bedroom in Sisters

Located in the heart of Sisters, Oregon. This brand new top floor (2nd story) condo is steps away from the main street of Sisters. Cozy and brand new, this space will have everything you need for your getaway. Fully equipped kitchen, with all the essentials.

Indoor spaces · Kitchen · Comfort