Family-friendly vacation rentals in Madras

Guest suite in Prineville

A spacious bedroom is furnished with a wooden sleigh bed topped with neutral linens and a decorative black blanket. Two bedside lamps illuminate the room. A stylish folding screen provides privacy, and large windows offer scenic views of the valley.

4.94 out of 5 average rating, 248 reviews

Artsy Guest House Nestled in the Rimrock

This property is truly an oasis from the hustle and bustle of city life. When you arrive, the massive rimrock wall will greet you; it is home to abundant wildlife (owls, deer, coyotes oh my). Shrouded by silence, the trill of frogs will put you to sleep. Mornings start with sunrise over the Ochoccos and full views of the valley and the crooked river at its base. Take a hike at Smith Rock, visit the Painted Hills or find yourself headed to town (Bend: 45 min, Prineville: 10 min, Redmond: 25 min).

4.98 out of 5 average rating, 905 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!

4.93 out of 5 average rating, 394 reviews

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

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.

4.83 out of 5 average rating, 628 reviews

A spacious living and dining area features a comfortable leather couch and a stylish patterned loveseat. A wooden dining table with chairs and a coffee table complete the seating arrangements. Natural light enters through the window and glass door, illuminating the space.

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.

4.95 out of 5 average rating, 1,181 reviews

A two-story apartment building is set against a vibrant blue sky, surrounded by lush greenery and landscaping. The structure features a warm color palette, with large windows and a wooden deck. A landscaped garden with various plants is visible in the foreground.

Apartment in Bend

Private apt, 1bdrm/1bath, with kitchen, in town

Brand new remodeled apt 2024! 1 king bed, 1 bath/shower with living/dining/bdrm/full kitchen apt. Private entrance. 3 bright, light & spacious rooms, treetop views. Kitchen has new full-size induction range and refrigerator, plus all cooking essentials. All new flooring/furnishings. Deck. In town location. Walking distance to NW Crossing, Newport Market, Galveston, also downtown Bend. Cycling routes just outside front door. Phils trails 2 miles. NOTE-28 steps up from street! NO pets allowed!

4.97 out of 5 average rating, 510 reviews

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

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

A welcoming outdoor fire pit area is surrounded by several wooden Adirondack chairs, inviting relaxation. Soft grass covers the yard, leading to a spacious home with large windows. Potted plants add color and life to the scene, while a clear sky transitions from daylight to evening.

4.98 out of 5 average rating, 289 reviews

Have a Patio Barbecue at a Pet-Friendly House in Midtown

Stoke the wood stove with another log and stay warm and cozy in a colorful plant-filled living room with stylish mid-century modern furniture. When the weather's nice, go outside to play croquet or corn toss and roast mores around the fire pit under the stars. Each bedroom has cable TV....large fully fenced in yard . Dogs are welcome. Limit of 3 with a $35.00 Pet fee. No cats allowed. Wood provided. There is a smart lock on the front door, you will be given the code before arrival.

4.87 out of 5 average rating, 430 reviews

The living area features a brick fireplace as a focal point, surrounded by comfortable seating options. A coffee table sits in front of a couch with a soft throw. Natural light enters through large windows, and a door leads to the exterior.

Home in Redmond

The Little Red Chimney House - 3 BR 2 BA

Originally built in 1944, this is a wonderfully furnished bungalow with 3 queen bedrooms and 2 full bathrooms, which I completely renovated and remodeled. It is a stone's throw from Fred Meyers grocery store and Cascade Lakes Brewery, and within easy walking distance to downtown. This house is at the hub of Central Oregon and sits at the crossroads between Bend (14 miles), Prineville (20 miles), and Sisters (20 miles) and is 10 miles from Smith Rock and 2 miles from the Airport.

4.96 out of 5 average rating, 462 reviews

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

Home in Terrebonne

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

4.98 out of 5 average rating, 306 reviews

A log cabin with a large front deck extends to the outdoors, surrounded by natural landscaping. The structure features a sloped roof and large windows that invite ample sunlight. Tall trees and rocky terrain complement the tranquil setting.

Cabin in Terrebonne

Steelhead Falls Log Cabin

Enjoy a restful time in our waterfront log cabin along the Deschutes River. Location is perfect for watching wildlife, fly fishing, quiet relaxation, and has easy access to hiking and rock climbing at Smith Rock and Lake Billy Chinook. Steelhead Falls is a a short hike away. Bend and Sisters are near. Unfortunately, we cannot accommodate even small weddings. We recommend access to AWD vehicle with either chains or snow tires in winter. Dog friendly- sorry, no cats.

4.97 out of 5 average rating, 323 reviews

A chalet with large glass windows allows natural light to fill the living spaces. The outdoor deck features seating under a large umbrella, surrounded by lush green grass and rocks. The evening sky presents a gradient of colors as dusk approaches.

Chalet in Redmond

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. DCCA# 1453

4.93 out of 5 average rating, 743 reviews

A cozy sleeping area features a wooden bed frame with a patterned grey comforter. A large armoire stands against the wall, and a small lamp is positioned on a bedside table. Light is infused into the space from a nearby window, creating a bright ambiance.

Guest suite in Bend

Orchard District Studio

A cozy studio apartment; this converted garage space has tall ceilings making it feel light and airy. Located in Bend's Orchard District, it is walking distance to Hollinshead Park & Pilot Butte. We are NOT within walking distance to downtown, however it is only a 5 minute drive to downtown & 15 minutes to outdoor recreation opportunities. Hosts live in the main house. LGBQT+ BIPOC friendly.

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Popular amenities for Madras family-friendly rentals

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Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A quaint cottage exterior is surrounded by greenery, featuring a covered porch with steps leading to the front door. Vibrant landscaping includes flowering plants, bushes, and trees, enhancing the inviting atmosphere of the home.

4.95 out of 5 average rating, 418 reviews

Cozy, Pet Friendly, Hot Tub. Garage.

Superhost

An open living space is displayed, featuring sliding barn doors that lead to a bedroom. A large wall artwork of a bridge over a misty landscape adds depth, while a cozy armchair and a small ornate table create inviting seating options.

4.87 out of 5 average rating, 396 reviews

Charming east side house, with hot tub.

A spacious living room features hardwood floors and a cozy sectional sofa in green. A flat-screen TV is mounted above a brick fireplace, while a round coffee table sits on a plush area rug. Natural light streams through large windows, illuminating the welcoming space.

4.84 out of 5 average rating, 125 reviews

NW Awbrey, Downtown, Steps 2 Park, Deschutes River

A two-story wooden house is set against a clear blue sky, featuring a spacious balcony with seating. The front area includes a tidy driveway, basketball hoop, and outdoor seating. Surrounding greenery adds to the natural setting.

4.94 out of 5 average rating, 132 reviews

20 acre ranch Bend Or

4.97 out of 5 average rating, 214 reviews

The vibrant yellow exterior of the home stands out against lush greenery and soft landscaping. A set of stone steps leads to a welcoming front porch, adorned with a warm glow from pendant lighting. Decorative shrubs and grass create a serene entrance path.

Home in Old Bend

Lava Flo, Historic gem on Lava Road, pets, hot tub

4.95 out of 5 average rating, 890 reviews

Apartment in Bend

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

4.95 out of 5 average rating, 184 reviews

The spacious great room features a comfortable sofa and contemporary armchairs arranged around a rustic coffee table. A dining area with a large window overlooks the outdoors, while wooden beams and cabinetry add warmth to the inviting atmosphere.

Townhouse in Bend

Points West 4 BR/4BA on Widgi near Seventh Mtn Res

4.91 out of 5 average rating, 479 reviews

A charming cottage is framed by flowering trees, featuring a welcoming front porch with seating. Stone accents and greenery enhance the entry, while large windows invite natural light into the home. The pathway leads through well-maintained landscaping, creating an inviting atmosphere.

Bungalow in Bend

Second Street Bungalow Dog Friendly/Walk Downtown

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Family- and pet-friendly home rentals

4.96 out of 5 average rating, 256 reviews

A tranquil country road stretches into the distance under a clear blue sky, featuring a vibrant double rainbow arching above. Fenced pastures are visible on either side, with patches of grass and dried earth. The road is wet, reflecting the colors of the rainbow.

Guesthouse in Bend

Quiet peacful country living close to everything!

A bright bedroom is showcased, featuring a spacious bed with crisp white linens. A wooden slatted headboard adds texture, while a small shelf holds books and a decorative plant. Natural light filters in, complemented by a minimalist artwork above the bed.

4.95 out of 5 average rating, 317 reviews

Westside Bungalow - Heart of Bend

4.94 out of 5 average rating, 421 reviews

The outdoor space features a fenced yard with a well-maintained grassy area, providing a private retreat. A gravel path leads to a patio area, which includes outdoor seating and a barbecue grill. Nearby structures contribute to a cozy, enclosed atmosphere.

Cottage in Bend

An Urban Base to Bend's Adventures!

A welcoming living space is depicted, featuring wooden cabinetry and a kitchenette equipped with an oven and microwave. A vibrant area rug enhances the wooden floor. A small dining table and chairs are visible, alongside a cozy couch and decorative throw pillows.

4.95 out of 5 average rating, 166 reviews

Separate Apt in Beautiful Westside Bend

4.96 out of 5 average rating, 187 reviews

An open loft space is depicted, featuring natural wood accents on the ceiling and a rustic ladder leading to a sleeping loft. A comfortable sofa sits next to a wooden coffee table, with a black refrigerator visible in the kitchen area.

Home in Old Bend

Bend River West Loft

4.96 out of 5 average rating, 158 reviews

A well-maintained two-story home is shown with light-colored siding and a neatly paved pathway. Lush green grass surrounds the entrance, which is adorned with vibrant flowering bushes. A small garage is visible on the right side of the house.

Home in Redmond

Large Group Comfort - 7 Separated Sleeping Areas!

A spacious outdoor area features a dining table and chairs, surrounded by natural stone landscaping and tall trees. A barbecue grill is positioned to one side, offering convenient cooking options. A shaded seating area invites relaxation, providing a comfortable environment for outdoor gatherings.

4.97 out of 5 average rating, 170 reviews

Old Mill Charm

4.95 out of 5 average rating, 351 reviews

A light-colored couch is positioned next to a vibrant area rug featuring floral patterns. A small dog sits on the polished hardwood floor. Exposed brick is visible near the kitchen area, which includes beige cabinets and a decorative wood-burning stove.

Cottage in Bend

Adorable West Side Cottage, Pet Friendly!

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Family-friendly home rentals with a pool

4.91 out of 5 average rating, 176 reviews

Chalet in Redmond

Eagle Crest Luxury Chalet w/Private Hot Tub&Garage

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.

4.97 out of 5 average rating, 218 reviews

Romantic Guest House w/Hot Tub, Pool, Tennis Court

4.93 out of 5 average rating, 242 reviews

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.

Home in Sisters

Private Peaceful Cabin in Sisters!

4.79 out of 5 average rating, 140 reviews

A spacious deck extends from the modern home, surrounded by tall pine trees. Large windows on the facade reflect natural light, while the deck space offers room for outdoor seating. The setting provides a sense of privacy and connection with nature.

Cabin in Sisters

Black Butte Ranch Family Style

4.92 out of 5 average rating, 131 reviews

An open living space features a well-equipped kitchen and a cozy seating area. Natural wood beams run across the ceiling, and rich wooden floors invite warmth. Comfortable chairs surround a central table, while a leather sofa and decorative artwork add character to the inviting space.

Cabin in Sisters

Red Clover Cabin at Black Butte Ranch

Superhost

A spacious outdoor swimming pool features clear blue water and is surrounded by multiple lounge chairs. Colorful play structures are visible in the background, along with trees providing shade around the pool area, creating an inviting atmosphere for relaxation.

Place to stay in Redmond

4.9 out of 5 average rating, 239 reviews

Cozy 2BR Townhome in Eagle Crest w/ Hot Tub!

4.94 out of 5 average rating, 248 reviews

The living area features a cozy leather sofa facing a mounted television. A wooden coffee table is centered on an intricately patterned rug. Two windows allow natural light to fill the space, complemented by light-colored walls and decorative elements.

Guest suite in Bend

Bungalow at The Parks