Family-friendly vacation rentals in Madras

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.

4.98 out of 5 average rating, 980 reviews

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 spacesKitchenAccuracy

4.92 out of 5 average rating, 129 reviews

A cozy living area features a grey sofa adorned with decorative pillows, positioned on a textured area rug. A flat-screen television is mounted on the wall, while a stylish black stove adds warmth. Natural light enters through a nearby window, enhancing the space.

Home in Redmond

Cozy Downtown Redmond Cottage

Welcome to our cozy Redmond cottage, located in the heart of downtown! Enjoy walking to local breweries, restaurants, and shops, all just steps away. This inviting space offers a perfect blend of comfort and convenience, ideal for couples or solo travelers. Unwind in the cozy living area after a day exploring Central Oregon. Experience the best of Redmond right outside your door! Conveniently close to: 15 minutes to Smith Rock 25 minutes to Bend 8 minutes to Deschutes County Fair & Expo Center

KitchenIndoor spacesParking

4.9 out of 5 average rating, 342 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!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

KitchenIndoor spacesNearby

4.84 out of 5 average rating, 708 reviews

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.

KitchenIndoor spacesNearby

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.

4.98 out of 5 average rating, 292 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

FamilyIndoor spacesBiking

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.

4.97 out of 5 average rating, 392 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.

FamilyKitchenCondition

4.9 out of 5 average rating, 294 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.

KitchenIndoor spacesAccess

4.94 out of 5 average rating, 167 reviews

A cozy tiny home with wooden exterior is set against a backdrop of lush greenery. A fire pit sits in the foreground, surrounded by open grass. A deck is visible, featuring a grill and seating area that invite outdoor relaxation.

Tiny home in Prineville

Tiny Pine house in the Ochocos at Wine Down Ranch

Cozy, country tiny home with deck, fire pit, views of meadows, and Ochoco National Forest. Interact with the horses, cattle, and dogs. Serene space with beautiful views of the Cascade mountains. Dark sky certified. View the Milky Way, many constellations, and a few galaxies. Located on 2100 acre Ranch, which is 11 miles from Prineville and 1 mile from the National Forest. Many outdoor activities are available - hiking, mountain biking, snowshoeing, birding, and much more.

FamilyIndoor spacesWalkability

4.97 out of 5 average rating, 241 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.

Apartment in Redmond

Cascade View Suite · Balcony · Smith Rock

Wake up to a wide Cascade Mountain view from this quiet upstairs studio on the rimrock, minutes from town. Step onto your private balcony, then head out to Smith Rock. Keypad self check-in, then settle into a space with recliners, fast Wi-Fi for remote work, and a smart TV. A mini split keeps it cool in summer and warm in winter. Big windows and a large closet. Sleeps two, with a roll-away for a third on request, small extra fee. Well-behaved, house-trained dogs are welcome.

Indoor spacesFamilyAccuracy

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.

4.97 out of 5 average rating, 517 reviews

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.

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 336 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.

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