Family-friendly vacation rentals in Madras

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Madras

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

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

4.97 out of 5 average rating, 184 reviews

Large Mountain View Suite on Quiet Acreage

Quiet rural location just a few miles from town on the rimrock above a small canyon. Enjoy a panoramic view of the Cascades from a spacious studio apartment that is comfortable and uncluttered. Features a roomy bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. Crib on request. Extra fee: 1) per pet 2) roll-away bed. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 mi

Guest favorite

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.

Guesthouse in Terrebonne

4.86 out of 5 average rating, 268 reviews

Near SmithRock pets ok low cost private cold ac

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Top guest favorite

A cozy living area features a spacious bed with a plaid bedding set, situated beside a large window that allows natural light to fill the room. A comfortable recliner sits nearby, complemented by rustic wood accents and a decorative area rug.

Ranch in Prineville

4.93 out of 5 average rating, 399 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

With 2100 acres nestled against the Ochoco NF, our ranch is a family-owned working ranch. Dark sky certified. Amazing view of the Milky Way and stars. Scenic meadows, managed forest lands, and rock vistas make up the landscape. Enjoy the slow-paced country lifestyle in an authentic ranch setting with horses, cows and dogs. Guests are welcomed and encouraged to enjoy the whole property. Many hiking areas and views to explore. Usual snowy winters make great fun for cc skiing and snow shoeing.

Top guest favorite

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

4.99 out of 5 average rating, 519 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.

Top guest favorite

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

4.98 out of 5 average rating, 248 reviews

Smith Rock Gardens

You'll enjoy the main house with the best views of Smith Rock and the Cascade mountains. Smith Rock State Park is literally across the street. A great location for outdoor activities at the park or in the region. Hike, climb, bike, walk or jog around the park. Sip tea inside and watch the animals. Perfect for artist and photographers. Relax on the deck or enjoy a sunset BBQ with gorgeous views. Owners live in adjoining unit. Separate entrance. Instagram: @smithrockgardens DCCA Tax# 1784

Guest favorite

The exterior of a two-story home is depicted, featuring a dark blue facade complemented by light trim. A set of wooden stairs leads to the main entrance, surrounded by landscaped rocks and plants. Multiple windows allow natural light to enter.

Guest suite in Redmond

4.93 out of 5 average rating, 299 reviews

Spacious and Private Suite in Central Oregon!

Want a spacious, private, comfortable, and clean place to stay for the weekend or business trip with great discounts for week + stays? This might be the place for you! The space is a sports themed, super clean, private living room, bedroom and bathroom near great Central Oregon attractions such as Smith Rock (12mi), Bend (14mi), and Sisters (18mi)! Deschutes County Expo Center and Redmond/Bend airport are within 4 miles. Guests enjoy a private entrance/exit and contactless check in/out!

Guest favorite

A spacious outdoor deck is furnished with two Adirondack chairs facing a circular fire pit. A panoramic view of distant mountains and valleys is framed by a railing, showcasing the landscape under clear blue skies.

Apartment in Redmond

4.97 out of 5 average rating, 520 reviews

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

Top guest favorite

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

4.97 out of 5 average rating, 308 reviews

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.

Top guest favorite

A spacious living area features large glass windows that provide views of the surrounding landscape, including trees and open fields. Comfortable seating with brown leather upholstery is arranged around a central coffee table. Natural light fills the room, highlighting the modern design.

Home in Terrebonne

4.99 out of 5 average rating, 278 reviews

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

Top guest favorite

A spacious living area features two comfortable sofas adorned with colorful decorative pillows. A coffee table sits in the center, and a large bed is positioned in the background, draped in a bright quilt. Natural light floods through large windows, illuminating the open space.

Guesthouse in Bend

4.98 out of 5 average rating, 419 reviews

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Top guest favorite

The entrance features a vibrant coral door framed by stone accents, leading into the guest house. A small welcome mat is placed before the door. Red Adirondack chairs are positioned nearby, and green and gray plants add a natural touch to the patio area.

Guesthouse in Terrebonne

4.98 out of 5 average rating, 182 reviews

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

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

4.85 out of 5 average rating, 226 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"