Family-friendly vacation rentals in Sisters

4.98 out of 5 average rating, 969 reviews

The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.

Home in Terrebonne

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!

4.97 out of 5 average rating, 377 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

Home in Terrebonne

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.

4.99 out of 5 average rating, 413 reviews

A yurt sits peacefully by a tranquil pond, surrounded by lush greenery and tall trees. Two wooden chairs are positioned on a small deck overlooking the water. The sky is painted in soft pastel hues as the sun sets, creating a serene backdrop.

Yurt in Bend

Yurt at Rainbow Ranch: Quiet, Cozy and Luxurious!

Looking for a quiet, cozy stay in a luxurious yurt? Well, then look no further than the Rainbow Ranch! We are located fifteen miles from Bend and a ten minute drive from Sisters. Whether you're seeking a place to land after an adventurous day or looking for a unique spot to unwind, you’re sure to cherish your time here. Enjoy views of the Sisters and Broken Top from the property by day. Then, snap a few photos of the glorious sunset, sit back, and watch as the stars light up the night sky.

4.9 out of 5 average rating, 283 reviews

A studio cabin is positioned on a deck overlooking a canyon, surrounded by native plants. Two wooden chairs are placed on the deck, providing a space to absorb the expansive mountain views in the distance. The structure features a large window reflecting the evening light.

Cabin in Culver

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.

4.87 out of 5 average rating, 119 reviews

The exterior of the newly built condo is showcased, featuring a well-maintained landscape with colorful shrubs and flowers. Paved walkways lead to the entrance, framed by trees. The modern architecture includes a combination of stone and wood accents, enhancing the inviting curb appeal.

Condo in Sisters

Views! 1 Blk to Town,New+Spotless, pets ok- North

Prime safe Sister's upscale neighborhood! Newly built condo offers EVERYTHING you expect without sacrificing a thing! Perfect INTERNET/WI-Fi and ONLY 1 BLOCK to downtown, restaurants, shopping. Leave your car at the unit and walk! Nice kitchen, king size bed in master, new queen size sofa/sleeper in living room! Relax on sofa or recliner w/ EXCELLENT Wi-FI, internet, cable, Netflix. Washer and dryer too! $35.00 pet fee PER pet under 40 lbs for the stay, Limit 2 pets.

4.94 out of 5 average rating, 208 reviews

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!

The exterior of a cozy, modern home is framed by tall trees and shrubs, providing a natural ambiance. A welcoming front porch features a bench, while warm lighting enhances the inviting appearance. A wooden fence borders the property, creating a sense of privacy.

4.93 out of 5 average rating, 103 reviews

Downtown Sisters Modern Home Ideal Location! Dogs!

Walk to all the great restaurants, shops, and parks from this perfect downtown location. Even the creek is only a short walk away. Your family and friends will love sitting in the backyard outdoor living area. This cozy newer home has three upstairs bedrooms and one small downstairs bedroom. If you want your next Sisters vacation and outdoor adventure to be in a comfortable single family home but in proximity to everything the town has to offer this property is for you

4.87 out of 5 average rating, 427 reviews

A cozy living area is seen, featuring a dark sofa against the wall, a coffee table, and a flat-screen TV mounted nearby. The kitchenette includes dark cabinetry, a microwave, and a mini fridge. A clock on the wall and ample natural light enhance the space.

Townhouse in Sisters

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.

4.95 out of 5 average rating, 133 reviews

The open living area features two brown leather couches and a large coffee table set on a patterned rug. A flat-screen TV sits on a white media console. Bright natural light enters through multiple windows, creating a welcoming atmosphere that connects to the dining area.

Condo in Sisters

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!

4.98 out of 5 average rating, 204 reviews

A charming cottage exterior is depicted, featuring a white picket fence and a welcoming covered porch. Lush green grass surrounds the house, complemented by tall trees in the background. A hanging plant basket adds a touch of greenery, enhancing the inviting entrance.

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

“Escape to the magical 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 dark night skies. Multiple decks, a covered gazebo with warm ambient lighting, and a private sauna await you.”

Superhost

An inviting open living space features large windows that allow natural light to fill the room. A dark grey sofa is arranged in front of a light wood coffee table, while a dining area with a long table is visible in the background. The kitchen includes wooden cabinetry and modern appliances.

4.83 out of 5 average rating, 175 reviews

Downtown Sisters - Juniper 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.

A comfortable living area is highlighted by a large sectional couch adorned with soft pillows. A wood stove provides warmth, while multiple windows offer views of the surrounding Ponderosa Pine forest. A coffee table holds a decorative tray, contributing to the cozy ambiance.

4.94 out of 5 average rating, 263 reviews

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.

Popular amenities for Sisters family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of the Cozy Hideaway features a red cabin with a covered deck supported by wooden beams. A hammock is seen on the deck beside a hot tub, surrounded by a natural landscape of pines and grassy areas.

4.93 out of 5 average rating, 163 reviews

Cozy Hideaway w/outdoor living and hot tub!

4.95 out of 5 average rating, 146 reviews

The front exterior of the newly constructed home features a welcoming entrance with large glass doors framed by warm lighting. A landscaped pathway of stones leads to the entrance, surrounded by gravel and desert flora, under a colorful twilight sky.

Home in Bend

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

4.99 out of 5 average rating, 149 reviews

A spacious living area features a sectional sofa in neutral tones, accompanied by a soft area rug. A stone fireplace adds warmth, while large glass doors open to a private balcony with outdoor seating. Natural light fills the room, enhancing the inviting ambiance.

Condo in Sisters

Beautiful Sisters Condo - Great location

The cabin features a welcoming entrance with a wood deck and rustic details. Framed by green trees, the two-story structure showcases a steep gabled roof and large windows, providing a warm and inviting sight. A path leads to the entrance, surrounded by low shrubs.

4.96 out of 5 average rating, 171 reviews

Pet + kid friendly w/ private hot tub!

An illuminated hot tub with turquoise water sits in the foreground, surrounded by trees. Warm string lights hang above, casting a soft glow over the outdoor seating area, which includes two chairs and a table, creating a cozy atmosphere for relaxation.

4.93 out of 5 average rating, 123 reviews

XL Hot Tub, Dog Friendly, EV Charger, Fenced Yard

Home in Black Butte Ranch

4.75 out of 5 average rating, 118 reviews

Hot tub. Golf. Wood fireplace. Resort Access.

4.89 out of 5 average rating, 228 reviews

A welcoming living area features a gas fireplace set within a brick surround. Large windows provide natural light and views of the outdoor space. A comfortable seating arrangement includes a dark sofa and a coffee table, while a bookshelf is filled with various books.

Townhouse in Sisters

Sisters Getaway

4.9 out of 5 average rating, 319 reviews

An A-frame interior features warm wooden paneling, with a cozy seating area highlighted by a stylish armchair and a television unit. The open door reveals a view of the outdoor pathway, surrounded by greenery, bringing natural light into the space.

Tiny home in Bend

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 159 reviews

A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.

Cottage in Redmond

Blossom Cottage Studio

4.95 out of 5 average rating, 586 reviews

A rustic log cabin is nestled among tall pine trees, featuring a welcoming porch with wooden railing. Sunlight filters through the branches, illuminating the surrounding forest floor and creating a serene atmosphere in the natural setting.

Cabin in Bend

Log Cabin on Tumalo Creek

4.95 out of 5 average rating, 736 reviews

The rustic log cabin features a sloped roof and is adorned with warm, soft lighting along the porch railing. Surrounding trees create a natural setting, and the cabin's windows are illuminated, suggesting a cozy and inviting environment.

Cabin in La Pine

Rustic Little Log Cabin In The Woods

4.94 out of 5 average rating, 254 reviews

An A-frame cabin is set against a colorful sunset, showcasing warm lights illuminating the exterior. The front entrance features a door with a welcoming window, while two rustic chairs sit on the porch, accompanied by potted plants and neatly stacked firewood.

Cabin in Bend

Black Duck Cabin

4.84 out of 5 average rating, 274 reviews

A colorful hammock is suspended from a snow-covered tree, inviting relaxation. The quaint WeeHouse, featuring large windows and a bright yellow door, is partly obscured by the snow. A serene winter landscape surrounds the property, showcasing the tranquility of the setting.

Tiny home in Bend

IT'S A WEE HOUSE

4.94 out of 5 average rating, 126 reviews

Cozy family cabin in Sisters, Central Oregon.

Superhost

A spacious living area features a wooden ceiling and tiled flooring. Comfortable seating options include a couch and armchair. A patterned rug adds color, and a coffee table sits centrally. The dining area and kitchen are visible in the background, with a staircase leading to the upper level.

Farm stay in Sisters

4.82 out of 5 average rating, 157 reviews

The Casa at the Red Barn Farm

4.92 out of 5 average rating, 236 reviews

A private outdoor area features a hot tub surrounded by string lights, creating a cozy ambiance. A wooden table displays a bottle of sparkling wine with two glasses and a small potted plant, inviting relaxation and enjoyment in nature.

Cabin in Bend

Eco cabin near Bend: sauna, spa, king bed, EV plug

Family-friendly home rentals with a pool

A two-story home situated among tall pine trees, featuring a warm, neutral exterior. The driveway leads to a wooden staircase that connects to the front entrance. The surrounding landscape is covered in soft pine needles and natural earth tones.

4.94 out of 5 average rating, 105 reviews

Large Black Butte Home With Private Hot Tub

4.98 out of 5 average rating, 252 reviews

A private patio features a bubbling hot tub and an umbrella table with chairs. Nearby, a gas grill is positioned for outdoor cooking. Soft lighting enhances the space, while large windows offer views into the cozy interior.

Home in Bend

Romantic Guest House w/Hot Tub, Pool, Tennis Court

The exterior of a charming townhome is presented, featuring a blend of textured siding and stone accents. A covered porch with wooden railing invites relaxation, while landscaped greenery and a stone pathway enhance the entrance. Large windows allow natural light to illuminate the space.

5 out of 5 average rating, 39 reviews

Beautiful Townhome with Patio

Cabin in Crooked River Ranch

4.93 out of 5 average rating, 133 reviews

Classic Cozy Cabin with Awe-inspiring Views

4.99 out of 5 average rating, 210 reviews

An aerial view captures the expansive property featuring a lush English Country Garden filled with vibrant flowers and greenery. A serene swimming pond is visible in the foreground, while the well-maintained guest suite is framed by trees in the background.

Guest suite in Bend

Luxurious Private Tumalo Suite Nestled in Trees

4.9 out of 5 average rating, 30 reviews

Walk to Downtown with Pool, Hot Tub + more access

A modern home is surrounded by snow-covered trees, showcasing large windows that reflect natural light. The wooden exterior complements the winter landscape, while steps lead from the porch to the yard blanketed in fresh snow.

4.92 out of 5 average rating, 136 reviews

Black Butte Ranch Home with THE View

Superhost

A cozy living space features a comfortable gray sofa with decorative pillows, a wooden coffee table, and a dining area with a table and chairs. Natural light fills the room through tall windows, illuminating the rustic wooden accents and equipped kitchen in the background.