Family-friendly holiday rentals in Black Butte Ranch

4.94 out of 5 average rating, 122 reviews

Cozy family cabin in Sisters, Central Oregon.

Relax with the family at this peaceful well appointed spacious cabin 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!

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.

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

Located in Black Butte Ranch, this recently updated 1970s vintage cabin has all the modern comforts of home. Smart TV, WiFi, BBQ Grill and cozy fireplace. This 975sq.ft cabin boasts an efficient and comfortable floor plan. Two bedrooms and one bathroom on the main with 3rd bedroom in semi-private loft upstairs. New appliances and necessary cooking staples in the kitchen. We do our best to keep it stocked with common spices, oils and condiments. 2pm Check-In!! Resort fees Included in my rate!!

4.9 out of 5 average rating, 165 reviews

The exterior of the cabin is surrounded by lush grass and tall trees, featuring a combination of natural wood doors. A large window allows light into the interior, while two chairs offer a place to relax outdoors.

Cabin in Camp Sherman

Camp Sherman Oregon Private Cabin Mt Jefferson

Small Cabin located near Lake Creek Lodge and Fire Station/Community Hall on the main road into Camp Sherman. This cabin is located on 1 acre property with grass and park area that includes, campfire area, horseshoe pit and pond (no swimming). Bike & hike trail adjacent to the store /river Perfect getaway, great condition with granite island and counter tops, knotty alder cabinets. Over 300 DVD collection. Wi-Fi Starlink, if remote working is necessary. GUESTS MUST CLEAN THE CABIN!!!

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.

4.92 out of 5 average rating, 138 reviews

Red Clover Cabin at Black Butte Ranch (+Hot Tub)

IDEAL LOCATION for the perfect Black Butte getaway! Well cared for, fully stocked, tastefully updated cedar cabin just feet from Paulina Pool and Springs! Hot tub with privacy screen. Miles of trails and endless opportunity for adventure and relaxation - just out the door. Well maintained, very CLEAN and organized. Open, user friendly kitchen/Great Room area. Large deck with BBQ under tall Ponderosa Pines. Pets welcome! 3 bedrooms, 2 full baths. Heat and AC. Perfect for up to 6-8 Guests.

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!

4.92 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

With a view like no other, you’ll be able to slow down, take it all in and press reset. You’ll be centrally located with an unobstructed view of the magnificent meadow. Floor to ceiling windows will have you gazing DIRECTLY at beautiful Black Butte throughout your stay. *Effective 1/1/24: All posted rental rates include your resort fee that Black Butte Ranch Resort charges for access to the resort amenities. Homeowners remit payment to the resort and do not retain any of this fee.

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, 133 reviews

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.

Home in Sisters

Black Butte Ranch Family Friendly Home Sleeps 14

Spacious Family Custom Built Vacation Home | Bike or walk to pools Close to Glaze Meadow pools Professionally cleaned and sanitized for you Open floor plan, large custom kitchen Things you'll love: ~ Shared pools and Hot tub ~ 2 Champion 18 hole Golf course ~ Spa ~ Lots of Natural light ~ 7 bikes & bike trailer at house ~ Bike paths ~ Snuggle wood stove on cool evenings ~ Children's books, games ~ 2 King Bedrooms ~ Bunk room ~ TV Netflix ~ Patio ~ BBQ Grill

Superhost

Home in Black Butte Ranch

4.74 out of 5 average rating, 111 reviews

Hot tub. Golf. Wood fireplace. Resort Access.

This multi-level home in Black Butte Ranch has a beautiful wrap-around deck & private hot tub. There are 3 bedrooms, 2.5 baths, and a loft entertainment area with a sofa bed. The space is open and bright with vaulted wood ceilings and large windows. The double-sided wood fireplace can be enjoyed from both the cozy living room and dining area.

Popular amenities for Black Butte Ranch family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 323 reviews

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.

Guest suite in Bend

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.

Apartment in Sisters

Renovated Sisters Condo; perfect getaway!

4.93 out of 5 average rating, 131 reviews

Cottage in River West

Old Mill Charmer with Hot Tub

4.96 out of 5 average rating, 117 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

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

4.9 out of 5 average rating, 203 reviews

An open living area showcases a large wooden dining table with black chairs, accompanied by a cozy seating arrangement featuring a light-colored sofa and a dark sectional. Tall windows provide natural light and views of the surrounding trees, while a modern ceiling fan enhances air circulation.

Home in Sunriver

Walk to SHARC 3BR Hot Tub

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.

Apartment in Sunriver

Sunriver Condo, 6 SHARC passes, pool, REC room

4.89 out of 5 average rating, 226 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

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, 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

4.92 out of 5 average rating, 613 reviews

A spacious studio apartment is shown, featuring a combination of cozy seating and a dining area. Natural light fills the room through glass doors that lead outside. A bed is visible in the background, creating a functional and inviting living space.

Guest suite in Sunriver

Pepper’s Place

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

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, 250 reviews

IT'S A WEE HOUSE

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!

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

4.94 out of 5 average rating, 265 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

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, 159 reviews

Cozy Hideaway w/outdoor living and hot tub!

Home in Black Butte Ranch

A spacious living area features large windows that frame views of the surrounding nature. Comfortable seating includes a leather sofa and plush chairs, while a stacked stone fireplace adds a cozy touch. Sliding doors open to an outdoor patio, enhancing the connection with the outdoors.

5 out of 5 average rating, 46 reviews

Black Butte Ranch Cabin on the 7th Fairway

4.87 out of 5 average rating, 23 reviews

The exterior of a cozy wooden cabin features warm red siding and large windows, offering ample natural light. A welcoming deck is adorned with two green chairs and a barbecue grill, surrounded by a grassy area and tall pine trees, creating a serene woodland setting.

Cabin in Camp Sherman

Creekside Studio Cabin at Lake Creek Lodge

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, 129 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.

Apartment in Sunriver

Beautiful Condo in SR Village

4.82 out of 5 average rating, 93 reviews

The spacious living area features a high ceiling with large windows providing views of the surrounding forest. A comfortable sectional sofa is positioned around a coffee table, while a dining table and kitchen area are visible in the background. A staircase leads to an upper loft space.

Home in Sisters

Serene Black Butte Ranch home: Shared pools & more

4.97 out of 5 average rating, 66 reviews

The living area features a spacious, dark blue sofa with a pull-out bed and a light wood coffee table. Soft natural light enters through large windows adorned with sheer curtains. A small accent chair and decorative plant complement the cozy ambiance.

Flat in Sisters

Peaceful Treetop Retreat-20 min to Hoodoo!