House holiday 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, 932 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!

Superhost

A modern farmhouse exterior showcases a two-story structure with a clean, white facade accented by dark windows and a covered porch. Two red chairs sit invitingly on the porch, framed by a gravel pathway and lush greenery.

4.94 out of 5 average rating, 196 reviews

Smith Rock Hideout - Cascade mountain views

The Hideout is a cozy and convenient base camp for climbers, hikers, trail runners, digital nomads, and anyone wanting to relax and explore the beauty of Central Oregon. Just 8 minutes to Smith Rock! Take in the views of the Cascade mountains and farmland beyond while relaxing on the covered porch. The Hideout is my personal semi-rural retreat. While away, I’m happy to share it with outdoor enthusiasts who enjoy creature comforts after a day of getting after it outdoors. Longer stays welcome!

A living area features a dark leather couch and a patterned armchair, centered around a wooden coffee table. Natural light filters through the window, illuminating the warm tones of the room. A landscape painting hangs on the wall, enhancing the inviting ambiance.

4.84 out of 5 average rating, 652 reviews

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.

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, 258 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

A spacious wrap-around deck is shown, featuring multiple comfortable lounge chairs facing expansive views of the surrounding landscape. Decorative string lights are hung overhead, adding a subtle touch. The distant mountains are visible against a clear blue sky.

4.97 out of 5 average rating, 184 reviews

Terrebonne~High Desert Hideaway~Near Smith Rock

Thank you for your interest in The Good Earth~High Desert Hideaway. In French Terrebonne means "Good Earth" & it is. Near the world-famous Smith Rock State Park, considered the cradle of US rock climbing. We are convenient to miles of the best hiking trails in Central OR. with views of the Cascade Mtn. Range from a large wrap around deck. An outdoor enthusiasts' paradise~5 mi. Smith Rock State Park, 5 mi. Steelhead Falls Trailhead, 25 mi. Sisters & 29 mi. Bend. Fish~Hike~Birdwatch~Climb

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.

4.98 out of 5 average rating, 326 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.

The exterior of the bungalow is shown, featuring a light blue facade with a welcoming front porch and a gravel pathway. Lush green grass surrounds the home, complemented by well-kept shrubs and trees. A clear blue sky enhances the inviting appearance of this charming property.

4.93 out of 5 average rating, 134 reviews

Downtown Redmond 3 bedroom

Welcome to this thoughtfully remodeled 80 year old Bungalow that rests in the heart of Redmond, Oregon. A 5 minute walk to fun local restaurants, breweries, bars, live music/concert venues, and eclectic shops. While this adorable home is a perfect vacation getaway, its location makes it very easy for you to get around. You are only: 10 mins to Cline Falls State Park 10 mins to the Redmond airport 10 mins to the Redmond Caves 15 mins to Smith Rock State Park 50 mins to Bachelor Ski Resort

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.

4.99 out of 5 average rating, 303 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.

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.

4.87 out of 5 average rating, 459 reviews

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.

The exterior of a charming cottage is displayed, featuring a well-manicured yard with flowering plants and shrubs. A welcoming porch with seating is visible, alongside large windows that bring in natural light. The driveway leads to a landscaped garden area.

4.93 out of 5 average rating, 235 reviews

Rhubarb Cottage - Entire house Dog Friendly!

Dog Friendly! Set in charming Old Town Redmond, this cottage has everything to offer for a quick weekend get away or longer stay with family. Only 25 minutes to downtown Bend and less than 10 minutes to the airport. Featuring 3 bedrooms, 2 full bathrooms, full laundry and a cozy kitchen! Gas bbq, expansive back patio, and corn hole boards to enjoy! Cruiser bikes available to ride to breweries or Dry Canyon Trail just minutes away. 2 Dogs max, additional cleaning fee applies.

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.

4.96 out of 5 average rating, 485 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.

A cozy living area features a leather couch facing a propane stove, with a warm fire flickering. Two wooden stools are positioned at a small table, and a stack of magazines is displayed on a wooden coffee table. Natural light filters through the window.

4.95 out of 5 average rating, 699 reviews

"Little Pine Cabin" attached to my home.

MASTER SUITE Go hiking, fishing, sight seeing and enjoy upscale steak houses, Sushi Bars, food carts, all within a couple of miles. Then come back to your Little Pine Cabin. Enter into a comfortable living area with a vaulted knotty pine ceiling, propane stove, a dual reclining leather couch. Relax in front of the 42 inch flat screen, a well stocked coffee bar, microwave and a mini-fridge. Similar to a studio apartment. You will enjoy the space and quiet neighborhood.

Popular amenities for Madras house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The living room features a stone fireplace surrounded by wooden shelves, with a large flat-screen TV mounted above. A rustic wooden coffee table sits on a patterned area rug, complemented by leather seating and large windows that allow natural light to flood the space.

4.98 out of 5 average rating, 126 reviews

Sunriver Luxury Family Home at Caldera Springs

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, 231 reviews

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

The exterior of the home displays a two-story structure nestled among tall trees. A wooden deck features a table and chairs, a barbecue grill, and an umbrella for shade, providing an inviting space for outdoor relaxation.

4.88 out of 5 average rating, 180 reviews

Sunriver home 8 SHARC passes, hot tub, wood stove

4.92 out of 5 average rating, 176 reviews

The exterior of the house is presented, surrounded by tall trees and foliage. A large paver patio is visible, featuring a barbecue and outdoor seating arrangements, all bathed in the warm hues of a sunset.

Home in Sunriver

Spacious 7BR Getaway, Golf View & Waterpark

4.94 out of 5 average rating, 261 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

A spacious great room features a large sectional sofa facing a sleek fireplace and a wall-mounted TV. Vaulted ceilings with wood beams create an open atmosphere. Expansive windows allow natural light to fill the space, showcasing views of the surrounding greenery.

4.96 out of 5 average rating, 123 reviews

Luxury Sunriver 5BR | 3 Suites! Hot Tub, EV, SHARC

4.93 out of 5 average rating, 123 reviews

The exterior of the modern home features dark blue siding and stone accents, set against a backdrop of tall pine trees. A well-paved driveway leads up to a two-car garage. A warm glow emanates from windows, hinting at the inviting interior.

Home in Sisters

Modern Tollgate Home - HOT TUB | Half Acre Lot

4.94 out of 5 average rating, 132 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

Weekly house rentals

4.98 out of 5 average rating, 164 reviews

A cozy master bedroom features a log queen bed with a green quilt. Two bedside tables with lamps provide soft lighting. A fan is positioned nearby, and a doorway leads to a bathroom area, emphasizing the spacious layout.

Home in Prineville

Visit Rip’s Cabin in the Heart of Prineville

The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.

5 out of 5 average rating, 282 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

A single-story house with a welcoming porch is framed by a gravel driveway. Lush greenery surrounds the entrance, complemented by blooming pink flowers. The cloudy sky adds depth to the scene, while large windows provide ample natural light. The structure features a simple, rustic design.

4.96 out of 5 average rating, 162 reviews

Deschutes River Escape *Clean + Modern*

4.99 out of 5 average rating, 204 reviews

The modern exterior of the ADU features wooden accents and large windows, surrounded by lush greenery. A small outdoor seating area with two chairs and a fire pit is visible. The entrance is framed by a wooden fence, providing privacy and inviting atmosphere.

Home in River West

Modern retreat in central Bend

A modern kitchen is showcased with a wooden countertop and several metal stools arranged in front. Open shelving holds dishware and kitchen essentials, while stainless steel appliances provide functionality. Large glass doors allow natural light to illuminate the space and offer views of the yard.

4.95 out of 5 average rating, 123 reviews

Dog friendly Home near parks and Dry Canyon

The exterior of a modern home is framed by blooming trees and shrubs, showcasing a gray exterior with large windows. A decorative pathway leads to the entrance, which features a covered porch. The driveway is spacious, providing easy access.

4.98 out of 5 average rating, 548 reviews

Home in Lodges at Bachelor View - Book Now!

An aerial view captures the proximity of the property to downtown Bend, with notable landmarks and tree-lined streets visible. The layout highlights a clear walking path leading to the town center, showcasing a mix of residential and commercial buildings amidst greenery.

4.99 out of 5 average rating, 318 reviews

"Urban Spruce" - Great peaceful location!!

A spacious living area features solid oak flooring and a wood-burning stove set against a stone wall. Large windows offer views of the surrounding trees and snowy landscape, while a cozy stack of firewood is arranged beside the stove.

5 out of 5 average rating, 189 reviews

Lava Rock Retreat Modern Rustic Home

Private house rentals

A spacious living area features a stone fireplace as a focal point, surrounded by comfortable seating. Wooden beams accentuate the high ceiling, while large windows offer views of the surrounding landscape. A coffee table is centered among the seating, with a rug beneath adding warmth.

4.94 out of 5 average rating, 50 reviews

Rock Ridge

4.94 out of 5 average rating, 36 reviews

A single-story house features a modern design with white siding and a black roof. Large windows allow natural light to enter. The front porch is adorned with potted plants. A garage door is visible to the right, and a gravel driveway offers ample parking space.

Home in Culver

L&T Chinook Properties

4.98 out of 5 average rating, 62 reviews

A cozy living room features a comfortable sofa, an accent chair, and a coffee table. A 60" smart TV is positioned across from the seating, while a large window allows natural light to fill the space. Decor includes a mirror and plants, enhancing the inviting atmosphere.

Home in Madras

Madras Oak House

A modern retreat is set against a backdrop of native landscaping, featuring expansive windows and a blend of wood and metal exterior. A winding path leads to a cozy fire pit area, surrounded by lush greenery and outdoor seating, providing a serene connection to the high desert environment.

5 out of 5 average rating, 21 reviews

Luxe 4BR/3BA • Smith Rock, 9 Peaks, Hot Tub, 10 Ac

4.98 out of 5 average rating, 62 reviews

The living area features a blue sectional sofa paired with light-toned accent chairs, creating a comfortable seating arrangement. A coffee table sits in front, and a workspace with a desk and chair is positioned nearby. Natural light enters through a window, enhancing the inviting atmosphere.

Home in Madras

Newly Remodeled 2BR Retreat with Private Backyard!

A cozy living room features a gray sectional sofa, offering ample seating. A modern round coffee table sits in the center, surrounded by a light area rug. Natural light filters through the window with a shade, complemented by a decorative table lamp and a large wall clock.

5 out of 5 average rating, 24 reviews

Entire home in Redmond