Family-friendly vacation rentals in Sisters

4.98 out of 5 average rating, 188 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

The cabin is nestled among tall trees, featuring a green exterior with a welcoming entrance. The front yard showcases natural grass and scattered pine needles, leading to a spacious driveway with a two-car garage on the right. Large windows provide an inviting view into the cabin.

4.94 out of 5 average rating, 122 reviews

Cozy family cabin in the tall pines of Tollgate.

Relax with the family at this peaceful well appointed sapcious cabin. 'Your Sisters Cabin' is located 3 miles from Downtown Sisters, 20 minutes to Hoodoo ski area and 10 minutes from Black Butte Ranch. We've geared the spaces towards fun and relaxation for the whole family! 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 beautiful fenced backyard, fully stocked kitchen, comfy beds and kid friendly amenities!

4.99 out of 5 average rating, 539 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.

4.84 out of 5 average rating, 667 reviews

A living area features a dark leather couch and a patterned armchair, centered around a wooden coffee table. Natural light filters through the window, illuminating the warm tones of the room. A landscape painting hangs on the wall, enhancing the inviting ambiance.

Home in Redmond

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

Guest suite in Orchard District

A bright room is illuminated by large windows with dark blinds. It features a spacious bed, a small table with two chairs, and a kitchenette area. A mini-fridge and microwave are visible, along with a lamp and a side table.

4.92 out of 5 average rating, 407 reviews

Midtown Getaway- Private entrance and bathroom!

Just over 2 miles from downtown. This is a private room attached to our house with a separate entrance. The room has a double bed, full private bathroom, closet space, a kitchenette, and seasonal access to the outside deck and hammock. Includes heating and cooling controls, a mini-fridge/freezer, microwave, coffee maker, cups, plates, and utensils. Coffee, tea, snacks, ice provided. Great for late night arrivals or early departures! The space is quaint- room & bathroom- 185 sq. ft. total

4.97 out of 5 average rating, 342 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.

4.97 out of 5 average rating, 155 reviews

The bedroom features a spacious bed with white linens, complemented by two bedside tables with lamps. A green bench sits at the foot of the bed, while a landscape painting hangs above the headboard. Soft curtains frame a window, allowing natural light to fill the space.

Guesthouse in Bend

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

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.

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, 151 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!

4.93 out of 5 average rating, 129 reviews

Modern Tollgate Home - HOT TUB | Half Acre Lot

This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you stay at this Tollgate home you get all of the community amenities with it: community pool, pickle-ball/tennis courts, walking trails, basketball courts, etc. Bring the whole family as we comfortably sleep 6 people and enjoy the hot tub! This is an incredibly well-done high-end modern home that is virtually brand new. We are also a dog friendly home ($100/stay fee).

Superhost

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

4.84 out of 5 average rating, 249 reviews

IT'S A WEE HOUSE

Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

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.

Condo 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.

Popular amenities for Sisters family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cozy living area features a comfortable gray sofa with colorful cushions and a wooden coffee table. Natural light fills the space through large windows, highlighting warm wooden accents. A flat-screen TV and bookshelf are positioned against the wall, offering convenience for relaxation and entertainment.

4.99 out of 5 average rating, 316 reviews

Private Apartment, Separate Entrance, Spacious

4.95 out of 5 average rating, 128 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!

4.98 out of 5 average rating, 945 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

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.

4.95 out of 5 average rating, 112 reviews

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

4.93 out of 5 average rating, 224 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

4.85 out of 5 average rating, 117 reviews

The exterior of the home displays a combination of dark blue siding and natural stone accents. A spacious front porch is featured, along with two garage doors and a wide paved driveway. The sloped roof adds to the home's structural interest.

Home in Redmond

Stunning mtn Views, sleeps 14, Hot tub, rec passes

4.95 out of 5 average rating, 924 reviews

The living room area features a red leather sofa and a small wooden coffee table, situated on a richly patterned area rug. A staircase with wooden railings leads to the upper loft. Natural light enters through windows positioned above, illuminating the space.

Apartment in River West

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

The living area features a spacious layout with a cozy seating arrangement, including a large armchair and a round ottoman. A wood-burning stove is positioned for warmth. The kitchen is visible, showcasing modern appliances and stylish wooden cabinetry, fostering a homey ambiance.

4.99 out of 5 average rating, 145 reviews

Ranch Cabin-2pm Check-In & no resort fees-Sleeps 4

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.

Apartment 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

4.94 out of 5 average rating, 160 reviews

A spacious living area is presented, featuring a large sectional couch and a leather ottoman. A wall-mounted television displays a scenic view. The dining area is visible in the background, showcasing a round light fixture above a table with four chairs. Light-colored walls enhance the bright atmosphere.

Townhouse in Larkspur

Bend Base-camp! Near river, mts, shops, fun stuff!

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

4.97 out of 5 average rating, 115 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

A spacious sleeping area features a large bed adorned with a patterned comforter and decorative pillows. Dark curtains frame a window that allows natural light to fill the room. Two nightstands with lamps are positioned on either side of the bed.

4.9 out of 5 average rating, 389 reviews

Cozy Studio! Walk to NW Crossing and Shevlin Park

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.

5 out of 5 average rating, 119 reviews

Sixties Suite Spot

4.98 out of 5 average rating, 268 reviews

A bright living space is highlighted by large windows allowing natural light to fill the room. Comfortable seating options, including a blue sofa and various chairs, are arranged around a rustic coffee table. A television stands in the corner, enhancing the casual atmosphere.

Home in Terrebonne

Smith Rock Gardens

Family-friendly home rentals with a pool

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.

4.86 out of 5 average rating, 257 reviews

Mt Bachelor Village Resort- Room in River Ridge II

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, 158 reviews

Cozy Hideaway w/outdoor living and hot tub!

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.

Condo in Bend

Adorable Studio at Seventh Mountain Resort

4.94 out of 5 average rating, 264 reviews

The open living space features a high beamed ceiling and natural wood accents. Two leather sofas are arranged around a light-colored coffee table. A dining area with a wooden table sits adjacent to the kitchen, which displays modern appliances and bar seating.

Home in Sunriver

A Little Peace of Paradise, A/C & 8 SHARC Passes

4.98 out of 5 average rating, 127 reviews

A spacious living area is furnished with a gray sectional sofa and a decorative coffee table, enhancing comfort and relaxation. A television is mounted on the stone fireplace wall, while an adjacent dining area features a round table with seating for four. Natural light floods through large windows.

Condo in Sunriver

Beautiful Condo in SR Village

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, 132 reviews

Black Butte Ranch Home with THE View

4.95 out of 5 average rating, 104 reviews

A spacious dining area features a wooden table surrounded by four chairs, with a decorative centerpiece of natural materials. A cozy living space can be seen in the background, highlighted by a stone fireplace and large windows allowing natural light.

Condo in Sunriver

Sunriver Condo, 6 SHARC passes, pool, REC room

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.