Family-friendly holiday rentals in Black Butte Ranch

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.

4.94 out of 5 average rating, 124 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!

4.98 out of 5 average rating, 957 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!

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, 146 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, 166 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 set amidst tall pine trees, displaying a striking black exterior. Tall, triangular windows allow natural light to brighten the interior. A spacious deck wraps around the cabin, offering an ideal spot for outdoor relaxation.

4.92 out of 5 average rating, 133 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!

4.97 out of 5 average rating, 359 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.

4.92 out of 5 average rating, 140 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, 159 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!

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, 134 reviews

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, 252 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.

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.

4.92 out of 5 average rating, 133 reviews

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

Home in Black Butte Ranch

4.75 out of 5 average rating, 114 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

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, 161 reviews

Cozy Hideaway w/outdoor living and hot tub!

4.93 out of 5 average rating, 236 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

4.92 out of 5 average rating, 217 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

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.

4.94 out of 5 average rating, 268 reviews

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

4.98 out of 5 average rating, 271 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, 158 reviews

A private outdoor deck features a hot tub positioned near the water's edge. Surrounded by tall trees, the area offers scenic views of the river and surrounding wetlands. Comfortable seating is available nearby for relaxation.

Home in Bend

Big River Getaway *Spectacular Riverfront Property

4.93 out of 5 average rating, 170 reviews

Home in Terrebonne

Smith Rock Oasis w/ Hot Tub Steps to the Park

A two-story home is surrounded by tall trees, showcasing a stone fireplace prominently on the facade. The expansive deck features wooden railings and an umbrella-covered seating area, framed by a clear blue sky with scattered clouds.

4.96 out of 5 average rating, 136 reviews

Comforts of home and fun for the whole family!

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 125 reviews

A spacious living area features a leather sofa and light wood flooring. A green table sits at the center, surrounded by white chairs. Natural light flows through large windows, illuminating the room, while a sliding barn door adds a rustic touch.

Cabin in La Pine

Green Forest Getaway - Modern & Cozy Cabin

4.93 out of 5 average rating, 121 reviews

Two blue Adirondack chairs are positioned on a lush green lawn, overlooking the calm Little Deschutes River. In the background, the river reflects the surrounding trees and grassy areas under a clear sky, creating a serene outdoor space for relaxation.

Home in La Pine

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

4.94 out of 5 average rating, 580 reviews

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.

Cabin in Bend

Log Cabin on Tumalo Creek

4.95 out of 5 average rating, 136 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, 169 reviews

A wooden dock extends over the clear waters of the Spring River, featuring a bright yellow kayak resting on the edge. A paddle lies nearby, and lush greenery surrounds the tranquil scene, providing a serene backdrop of trees and natural beauty.

Cabin in Sunriver

Riverfront Cabin w/ Private Dock & HotTub

4.96 out of 5 average rating, 268 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

4.9 out of 5 average rating, 328 reviews

A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.

Cottage in Terrebonne

Quiet central Oregon desert retreat with a view!

A spacious living area features a comfortable L-shaped sofa adorned with a light throw. Natural wood beams accentuate the ceiling, while a gas fireplace adds warmth. A flat-screen TV is visible, and a dining table with bar stools is situated nearby against neutral-toned walls.

4.85 out of 5 average rating, 119 reviews

Updated Sunriver-Hot Tub, Walk to SHARC & Village

Family-friendly home rentals with a pool

Superhost

The home is nestled among tall ponderosa pines, displaying a light-colored wooden exterior. A spacious front porch features two rocking chairs, inviting relaxation in a tranquil forest setting. The surrounding ground is covered in fallen pine needles, enhancing the natural atmosphere.

5 out of 5 average rating, 6 reviews

Woodzy Retreat Getaway

4.93 out of 5 average rating, 86 reviews

A spacious living area features wooden walls and a high vaulted ceiling. A large sectional sofa, a coffee table, and bean bags are arranged around a stone fireplace. Natural light enters through large windows, with artwork enhancing the wall. Wood logs are neatly stacked beside the fireplace.

Holiday home in Sisters

Acer Haus-Cozy, cool & dog friendly in Black Butte

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!

A warm living area features a vaulted wood ceiling, large windows allowing natural light to fill the space, and a stone fireplace as its focal point. Comfortable seating includes a sofa with plush cushions and a unique lamp, creating an inviting atmosphere.

5 out of 5 average rating, 39 reviews

Partridge Foot - 3BR, private hot tub, EV charger

The exterior of the home features a modern design with large windows that enhance natural light. A spacious deck equipped with comfortable red lounge chairs and a dining table provides an inviting outdoor space, surrounded by a natural landscape of tall trees.

4.97 out of 5 average rating, 34 reviews

BBR Golf View Home with grand fireplace & Hot Tub

An inviting living area features wood paneling and a vaulted ceiling, creating an airy ambiance. A small round dining table with four chairs sits beside a cozy seating arrangement, which includes a red couch and an armchair. Soft lighting enhances the warm atmosphere.

5 out of 5 average rating, 25 reviews

Cabin Retreat @ Black Butte Ranch Hottub

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, 143 reviews

Tollgate Cabin in the Pines (with Level 2 Charger)

A welcoming living area features a comfortable leather sofa and a round coffee table, surrounded by natural light from large windows. Nearby, various bicycles are arranged neatly against a garage. An indoor hot tub is set within a cozy wooden room, and a vibrant waterpark scene is visible, showcasing leisure activities.