Family-friendly holiday rentals in Sisters

4.99 out of 5 average rating, 154 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

Great location! Remodeled 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The hot tub/sauna are open year round. The club house includes ping pong, foosball and a pool table. You just need to walk through the city park and across the creek to get into town. We are also located about two blocks from the MovieHouse and Three Creeks Brewing. Enjoy bike paths close by and lots of hiking in the area. Easy self check-in and out.

Indoor spacesKitchenBiking

Superhost

A spacious outdoor deck is furnished with a table and several comfortable chairs, providing an inviting space for gatherings. An umbrella offers shade, while a grill is positioned nearby. The surrounding trees create a natural backdrop, enhancing the tranquility of the setting.

4.85 out of 5 average rating, 99 reviews

Perfect Home in the Pines with hot tub!

Relax with family and friends in this peaceful Sisters home. Cozy and open the home has a smart TV along with stainless steel appliances, classic decor, and a great outdoor area in the back with a fire pit, BBQ and furniture. Only a couple minutes to downtown Sisters and 15 mins to ski at Hoodo. Free pool access at the Tollgate seasonal pool, pickle ball courts, a tennis court, basketball court, children's playground and many acres of National Forest land for miles of mountain biking or hiking.

KitchenIndoor spacesAccess

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.

4.98 out of 5 average rating, 980 reviews

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!

KitchenIndoor spacesAccuracy

A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.

4.99 out of 5 average rating, 139 reviews

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!

KitchenIndoor spacesLaundry

The cabin is nestled among tall pine trees in a serene wooded setting. A two-car garage stands adjacent to the cabin, with ample outdoor space featuring a carpet of mossy ground cover. Sunlight filters through the trees, creating a peaceful ambiance.

4.95 out of 5 average rating, 128 reviews

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!

FamilyKitchenOutdoor spaces

4.99 out of 5 average rating, 422 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.

FamilyKitchenHospitality

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.

4.97 out of 5 average rating, 177 reviews

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!

FamilyIndoor spacesPets

4.9 out of 5 average rating, 294 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.

Indoor spacesFamilyAccess

4.92 out of 5 average rating, 213 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!

KitchenIndoor spacesOutdoor spaces

4.87 out of 5 average rating, 436 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.

FamilyIndoor spacesCondition

4.98 out of 5 average rating, 209 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 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.”

KitchenIndoor spacesCleanliness

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, 269 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.

Indoor spacesFamilyWi-Fi

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, 167 reviews

Cozy Hideaway w/outdoor living and hot tub!

Indoor spacesKitchenCleanliness

4.96 out of 5 average rating, 296 reviews

Guest suite in La Pine

Guest suite | Hot tub & sauna Cabin in the Woods

KitchenFamilyShared spaces

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.

4.95 out of 5 average rating, 155 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

FamilyKitchenBarbecue

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.

4.97 out of 5 average rating, 392 reviews

Pointe of Blessing with hot tub and canyon views

FamilyIndoor spacesHot tub

4.94 out of 5 average rating, 265 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

FamilyIndoor spacesDecor

4.98 out of 5 average rating, 284 reviews

The exterior of the chalet is showcased, featuring a peaked roof and large windows that allow ample natural light. A spacious wooden deck is present, accompanied by outdoor seating and a barbecue. The surrounding grassy area enhances the outdoor setting.

Chalet in Redmond

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

Indoor spacesFamilyGetting around

4.93 out of 5 average rating, 184 reviews

Smith Rock Oasis w/ Hot Tub Steps to the Park

KitchenFamilyBathroom

The exterior of a spacious home is shown, featuring a light brown facade and large windows that provide ample natural light. A wooden deck is visible at the front, furnished with several outdoor chairs, and surrounded by tall, green trees in a serene landscape.

4.93 out of 5 average rating, 137 reviews

Black Butte Ranch Family Friendly Home Sleeps 14

KitchenIndoor spacesHiking

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 133 reviews

A log cabin is surrounded by snow-covered pine trees, highlighting its rustic wooden structure. A balcony extends from the upper level, while lounge chairs are positioned in front of the cabin, creating a cozy outdoor space in a peaceful winter setting.

Cabin in La Pine

Modern-Cozy LOG CABIN near La Pine state park

KitchenFamilyParks

4.97 out of 5 average rating, 238 reviews

Butler Corner - New, Clean & Minutes From Downtown

FamilyIndoor spacesTV

4.85 out of 5 average rating, 379 reviews

A modern living area features a spacious gray couch and a dining table with white chairs. A vibrant abstract painting adds color to the wall, while a fully equipped kitchenette is visible in the background with blue cabinetry and natural light streaming through large windows.

Tiny home in Bend

The Big Tiny

Indoor spacesKitchenWi-Fi

4.85 out of 5 average rating, 290 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

FamilyKitchenValue

A wooden deck overlooks a serene river, flanked by lush greenery. Two comfortable armchairs with bright cushions are arranged around a small table, inviting relaxation and enjoyment of the peaceful environment.

4.84 out of 5 average rating, 474 reviews

River View Inn a cabin on the River

Indoor spacesFamilyDecor

4.9 out of 5 average rating, 330 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

KitchenFamilyAccess

4.91 out of 5 average rating, 161 reviews

A newly built condo complex features a charming entrance with front porches. Well-maintained landscaping includes colorful flower beds and green shrubs, framed by tall trees. The clear blue sky above casts a bright ambiance, accentuating the inviting architectural design.

Condo in Sisters

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

Indoor spacesKitchenLocation

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

4.97 out of 5 average rating, 517 reviews

Canyon House, Crooked River Ranch

FamilyIndoor spacesHot tub

Family-friendly home rentals with a pool

The exterior of a large two-story house is displayed, featuring a covered porch supported by columns. Lush green grass surrounds the structure, complemented by neatly arranged shrubs. A clear blue sky with soft clouds is visible above, enhancing the overall setting.

4.93 out of 5 average rating, 282 reviews

Updated Game Room! Hot Tub, SHARC (8), 2,800sq/ft

Indoor spacesFamilyValue

4.96 out of 5 average rating, 134 reviews

Townhouse in Sunriver

Newly Remodeled 3 bdrm-Hot Tub-SHARC passes-Bikes

FamilyIndoor spacesSkiing

4.95 out of 5 average rating, 138 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!

Indoor spacesKitchenQuiet

4.99 out of 5 average rating, 217 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

FamilyIndoor spacesBiking

4.96 out of 5 average rating, 137 reviews

An open living area is displayed, featuring a dark leather sofa and a wooden coffee table. A dining area with wooden chairs is seen in the background, along with a well-equipped kitchen that is partially visible. Natural light brightens the space, highlighting the warm wood flooring.

Townhouse in Redmond

Eagle Crest townhome Dog friendly-sleeps up to 6

FamilyIndoor spacesHospitality

An indoor pool room features a heated dipping pool, surrounded by vibrant red lounge chairs. A seating area is present with a couch and decorative pillows, while bright artwork adorns the walls. Sliding glass doors allow natural light and lead to the outside.

4.97 out of 5 average rating, 192 reviews

Indoor Pool, Spa, Game Room, Pets Welcome!

KitchenIndoor spacesBathroom

4.9 out of 5 average rating, 229 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

KitchenIndoor spacesCheck-in

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.