Family-friendly holiday rentals in Sisters

4.98 out of 5 average rating, 193 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.

Imagine yourself surrounded by majestic old-growth ponderosa pine and juniper trees, where the gentle murmur of Whychus Creek is in the distance, all while being just a short stroll from the vibrant heart of downtown Sisters. Embrace the tranquility as you explore an array of delightful restaurants, local festivals, and enjoy nearby parks, as well as endless hiking and biking trailheads, the Creekside campground, all within moments’ reach. Minutes’ drive to Hoodoo Mountain, Blackbutte, Aspen

4.99 out of 5 average rating, 137 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.

Apartment 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 a block or two 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.

4.99 out of 5 average rating, 542 reviews

A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.

Cabin in Bend

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

The modern A-frame cabin is surrounded by snow-covered trees, highlighting its dark exterior. A deck extends around the cabin, accentuated by a row of small evergreen planters against the backdrop of a winter landscape, showcasing the serene setting.

4.92 out of 5 average rating, 129 reviews

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

An open-plan living space features a wooden dining table surrounded by white chairs, complemented by a decorative plant in a pot. Natural light filters through a skylight and windows, enhancing the wooden beams and soft color palette of the room.

5 out of 5 average rating, 154 reviews

Modern Mountain Cabin Close to Town (HOT TUB!)

Come enjoy this beautiful home filled with tons of natural light, skylights, a cozy fireplace and a highly functional open floor plan. The backyard features a newly built deck and outdoor dining, BBQ, patio loungers, fire pit and HOT TUB! All the benefits of a quiet neighborhood while being just a 5 - 10 minute walk from the heart of downtown Sisters and a short drive to endless hikes and running trails, beautiful lakes and rivers, skiing, rock climbing, mountain biking and so much more.

4.97 out of 5 average rating, 101 reviews

A classic two-story home is presented against a vibrant sunset sky. The wrap-around porch features white columns and is surrounded by neatly trimmed shrubs. Large windows face the yard, allowing for ample natural light to enter the living space.

Home in Sisters

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.

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, 152 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!

4.89 out of 5 average rating, 242 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.

4.92 out of 5 average rating, 140 reviews

The exterior of the condo features a welcoming entrance, framed by vibrant landscaping. A covered porch with seating is visible, alongside manicured shrubs and decorative plants. Bright sunlight highlights the facade, creating an inviting atmosphere.

Apartment in Sisters

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

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.

4.98 out of 5 average rating, 286 reviews

A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.

Apartment in Bend

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

4.93 out of 5 average rating, 187 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!

4.87 out of 5 average rating, 408 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.

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, 159 reviews

Cozy Hideaway w/outdoor living and hot tub!

4.95 out of 5 average rating, 128 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

4.98 out of 5 average rating, 948 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

4.93 out of 5 average rating, 131 reviews

Cottage in River West

Old Mill Charmer with Hot Tub

4.95 out of 5 average rating, 113 reviews

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.

Home in Sisters

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

4.94 out of 5 average rating, 109 reviews

A cozy living area features large windows with sheer curtains allowing natural light. A stack stone gas fireplace serves as a focal point beside a TV unit. Comfortable seating options include a pair of sofas and a rustic dining table adorned with greenery.

Townhouse in Redmond

Creekside Luxury @ Eaglecrest-Dog Friendly Escape!

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, 155 reviews

The Casa at the Red Barn Farm

4.92 out of 5 average rating, 203 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- and pet-friendly home rentals

4.98 out of 5 average rating, 213 reviews

A small balcony is visible, featuring two woven chairs and a round blue table. Panoramic views of the surrounding landscape and distant trees can be seen, with clouds casting soft shadows over the scene and sunlight filtering through the open space.

Flat in Redmond

Mountain View Suite near Smith Rock + Airport

4.92 out of 5 average rating, 130 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

4.98 out of 5 average rating, 194 reviews

Home in Orchard District

Butler Corner - New, Clean & Minutes From Downtown

4.96 out of 5 average rating, 247 reviews

The cozy bedroom features a rustic wooden bed frame with soft linens, complemented by natural light from a nearby window. A stylish soaking tub is presented with a wooden shelf nearby. The kitchen showcases modern appliances with a striking blue cabinetry, while a snowy mountain landscape is displayed outdoors.

Home in Bend

Romantic Farmhouse near Mt. Bachelor

4.85 out of 5 average rating, 443 reviews

A snow-covered pathway leads to the guest suite, surrounded by tall evergreen trees. Snowflakes gently fall, creating a serene winter scene. The building features large windows that illuminate the entrance, offering a warm glow against the frosty surroundings.

Guest suite in Bend

Private Getaway | 20min to Bend & Adventures!

4.93 out of 5 average rating, 225 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

Guest house in Terrebonne

An open living space is visible, featuring a comfortable black couch with a plaid throw. A modern kitchen area with stainless steel appliances is seen, along with a dining table in the background. Warm wood flooring enhances the inviting ambiance.

4.86 out of 5 average rating, 286 reviews

Near SmithRock pets ok private heated bungalow

5 out of 5 average rating, 120 reviews

A cozy bedroom features a spacious bed with a colorful blanket, complemented by wooden accent walls. A wall-mounted flat-screen TV is above a modern electric fireplace. A small table with two chairs is positioned nearby, with a mirror framed in green accentuating the space.

Guest suite in Bend

Sixties Suite Spot

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 258 reviews

The room features a queen bed with a light-colored bedspread, accompanied by bedside tables with lamps. A cozy seating area with cushions is beside a large window, allowing natural light to illuminate the space. Artworks are displayed on the walls, enhancing the serene atmosphere.

Guest suite in Bend

Mt Bachelor Village Resort- Room in River Ridge II

4.9 out of 5 average rating, 145 reviews

A comfortable living area showcases a cozy sofa and a well-lit dining space with a light-colored table surrounded by colorful chairs. Natural light filters through the windows, illuminating the modern vinyl flooring and the stylish decor elements, including a wall-mounted TV above a decorative fireplace.

Apartment in Bend

Adorable Studio at Seventh Mountain Resort

4.97 out of 5 average rating, 239 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

4.98 out of 5 average rating, 127 reviews

A bright bedroom features a king bed adorned with colorful accent pillows. The walls are decorated with a simple mountain-themed mural, providing a modern touch. Soft yellow bedside lamps illuminate matching nightstands, while fresh flowers add a welcoming element to the space.

Apartment in Bend

Pool, AC, close to Amphitheater & Old Mill

Cabin in Crooked River Ranch

A row of rustic cabins is set against a natural backdrop, showcasing wooden exteriors and inviting porches. Each cabin features a distinct entrance, with picnic tables arranged on the deck. A gravel path leads through the surrounding shrubbery, offering a sense of tranquility.

4.93 out of 5 average rating, 125 reviews

Classic Cozy Cabin with Awe-inspiring Views

4.98 out of 5 average rating, 265 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 Eagle Crest

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

4.92 out of 5 average rating, 133 reviews

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.

Home in Sisters

Black Butte Ranch Home with THE View