Family-friendly vacation rentals in Sisters

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.

4.99 out of 5 average rating, 154 reviews

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 spacesKitchenWalkability

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.

4.81 out of 5 average rating, 101 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.

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 980 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!

Indoor spacesKitchenGetting around

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.

4.73 out of 5 average rating, 150 reviews

Tollgate Cabin in the Pines (with Level 2 Charger)

The cabin has three bedrooms and one full bathroom. The kitchen is stocked with a refrigerator, oven, microwave, toaster, coffeemaker, and cooking utensils. In the living room, we have a wood stove fireplace and board games. In the summer, guests will have access to the community pool. This is a rustic house, and is priced accordingly. We love the cozy feel of it and is quite comfortable. Please note that there is no AC, WiFi, TV, or music system...this is your chance to get away from it all.

Indoor spacesKitchenCheck-in

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.

4.99 out of 5 average rating, 574 reviews

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.

KitchenIndoor spacesParks

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, 129 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!

Indoor spacesKitchenWalkability

4.97 out of 5 average rating, 394 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.

KitchenIndoor spacesAmenities

4.9 out of 5 average rating, 298 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.

FamilyKitchenPets

4.95 out of 5 average rating, 193 reviews

A comfortable living area features a bright red sofa and an additional lounge chair. Natural light filters through large windows, highlighting the neutral wall colors and carpeting. A television is positioned on a sturdy stand, while a small dining table is visible in a corner.

Apartment in Sisters

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.

FamilyIndoor spacesHeating

4.93 out of 5 average rating, 216 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!

FamilyKitchenPets

4.87 out of 5 average rating, 438 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.

KitchenIndoor spacesBathroom

A serene bedroom features a spacious bed with white linens, flanked by two bedside lamps. Decorative art is displayed above the bed, with light streaming in through nearby windows. A sliding barn door adds a rustic touch, complementing the warm wood tones of the furniture.

4.94 out of 5 average rating, 253 reviews

Downtown Sisters- *New* 1 Bedroom Condo

Enjoy staying in the heart of downtown Sisters. Just two blocks from the Main Street, this brand new unit will have everything you need for your getaway. This bright and open condo is located on the second floor of a two story building. Featuring brand new furniture, queen mattress, appliances and a fully equipped kitchen. Explore all the wonderful surroundings in Sisters and come home and relax in this great space!

FamilyKitchenAccuracy

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 charming A-frame cabin is surrounded by tall pine trees, featuring a spacious front porch with two rocking chairs and a set of steps leading to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere.

4.95 out of 5 average rating, 96 reviews

Riverwoods A-Frame

FamilyKitchenCleanliness

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.

4.94 out of 5 average rating, 159 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

KitchenIndoor spacesLayout

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, 107 reviews

Large Black Butte Home With Private Hot Tub

KitchenIndoor spacesGrill

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, 180 reviews

Pet + kid friendly w/ private hot tub!

FamilyKitchenView

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.

4.94 out of 5 average rating, 268 reviews

Black Duck Cabin

FamilyIndoor spacesNearby

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!

FamilyIndoor spacesQuiet

4.89 out of 5 average rating, 332 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

FamilyIndoor spacesAccess

4.95 out of 5 average rating, 320 reviews

The main living area features natural wood paneling and a vaulted ceiling. A black sofa is adorned with a blanket, positioned beside a wooden coffee table on a light-colored rug. Nearby, a compact kitchen area is visible, along with a ladder leading to the loft.

Cabin in La Pine

Cozy Forest Cabin w/ Sauna & Hot Tub!

KitchenIndoor spacesComfort

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 299 reviews

Guest suite in La Pine

Guest suite | Hot tub & sauna Cabin in the Woods

FamilyKitchenLocation

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.

4.88 out of 5 average rating, 124 reviews

Views! 1 Blk to Town, Clean+Charming,pets ok-North

FamilyKitchenBathroom

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.

4.94 out of 5 average rating, 595 reviews

Log Cabin on Tumalo Creek

Indoor spacesFamilyBreakfast

4.97 out of 5 average rating, 241 reviews

Butler Corner - New, Clean & Minutes From Downtown

KitchenFamilyTV

4.88 out of 5 average rating, 566 reviews

The exterior features a wooden fence and walkway leading to Miss Clementine, the Airstream, with surrounding shrubs and trees providing a natural setting. A welcoming entryway is visible, framed by the rustic wood structure, emphasizing a blend of comfort and nature.

Camper/RV in Bend

Meet Miss Clementine-1973 Airstream w/Cozy Hot Tub

KitchenFamilyLocation

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.

4.95 out of 5 average rating, 322 reviews

Romantic Farmhouse near Mt. Bachelor

KitchenIndoor spacesOutdoor spaces

4.85 out of 5 average rating, 292 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

KitchenFamilyAccess

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, 478 reviews

River View Inn a cabin on the River

FamilyKitchenDecor

Family-friendly home rentals with a pool

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, 168 reviews

Cozy Hideaway w/outdoor living and hot tub!

Indoor spacesFamilyHot tub

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.

4.95 out of 5 average rating, 138 reviews

Renovated Sisters Condo; perfect getaway!

Indoor spacesKitchenLocation

The exterior of the home displays a two-story structure nestled among tall trees. A wooden deck features a table and chairs, a barbecue grill, and an umbrella for shade, providing an inviting space for outdoor relaxation.

4.89 out of 5 average rating, 209 reviews

Sunriver home 8 SHARC passes, hot tub, wood stove

KitchenFamilyCheck-in

A cozy living area features light wood paneling and large windows. A comfortable sectional sofa, accented with orange and gray pillows, is positioned on a plush area rug. A wood stove adds warmth, while a framed landscape artwork complements the natural tones.

4.8 out of 5 average rating, 159 reviews

Country House Condo with a View

KitchenFamilyGrill

5 out of 5 average rating, 9 reviews

Meadows' Edge at Black Butte Ranch

FamilyCleanlinessView

4.98 out of 5 average rating, 285 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!

KitchenFamilyBathroom

4.9 out of 5 average rating, 230 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

FamilyKitchenAmenities

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.