House vacation rentals in Madras

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Top-rated house rentals in Madras

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Guest favorite

Home in Terrebonne

4.98 out of 5 average rating, 812 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!

Oct 17 – 24

G$73,885 GYD per night

Guest favorite

Home in Terrebonne

4.97 out of 5 average rating, 166 reviews

Pointe of Blessing with hot tub and canyon views

We hope you will enjoy our Pointe of Blessing. We feel our canyon perch is a gift from God-just 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. Prepare to relax unwind and enjoy spectacular sunrises and moonrises.

Oct 17 – 24

G$35,970 GYD per night

Guest favorite

Home in Redmond

4.82 out of 5 average rating, 520 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.

Jan 7 – 14

G$19,767 GYD per night

Guest favorite

Home in Terrebonne

4.97 out of 5 average rating, 175 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

Jul 22 – 27

G$33,994 GYD per night

Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 172 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

G$41,464 GYD per night

Guest favorite

Home in Terrebonne

4.95 out of 5 average rating, 121 reviews

Smith Rock Nest - Steps to the Park!

No other home is closer to the Smith Rock's main attractions. The entire 3BR/2BA home in Terrebonne is yours for a perfect stay to maximize your Smith adventure! Enjoy the stocked kitchen, wood burning stove, central heat/AC, laundry, and hot tub. High speed fiber-optic internet and desk are provided for remote work. Discounts for week-long stays. Quick access to Bend (30 mins), Sisters (35 mins) and Mt. Bachelor (1 hour). No pets, no RVs, and no parties/events permitted. DCCA# 1715

Oct 9 – 16

G$57,712 GYD per night

Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 123 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.

Feb 3 – 10

G$63,693 GYD per night

Guest favorite

Home in Redmond

4.87 out of 5 average rating, 339 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.

May 28 – Jun 4

G$30,424 GYD per night

Guest favorite

Home in Redmond

4.93 out of 5 average rating, 131 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.

Jan 12 – 19

G$29,986 GYD per night

Guest favorite

Home in Redmond

4.97 out of 5 average rating, 236 reviews

Redmond Downtown Retreat

Nice, new home with all the amenities you need for a home-away-from-home stay with alley access and plenty of private parking for 2-3 cars. Centrally located, this home is an easy 2.5 miles to the Redmond airport, 3 miles to Deschutes County Fairgrounds and Expo Center, 15 miles to Smith Rock, 17 miles to Bend, and 20 miles to Sisters. It is an easy walk to several brew pubs and eateries, and to miles of paved and dirt trails, skate park, playground and tennis courts.

Jul 5 – 12

G$27,457 GYD per night

Guest favorite

Home in Terrebonne

4.95 out of 5 average rating, 140 reviews

Fallen Snag Lodge next to Smith Rock State Park

One mile from Smith Rock State Park & 30 minutes from Bend, Fallen Snag Lodge will be your very own private nature preserve. A wrap around deck faces the Marsupial rock formations & Crooked river, with lounge chairs set to view hawks, turkey vultures & eagles during the day & for stargazing at night. Ideal for couples or a family wanting to get away from it all in a beautifully appointed, comfortable lodge set in central Oregon's magnificent high desert landscape.

Dec 7 – 14

G$57,054 GYD per night

Guest favorite

Home in Terrebonne

4.99 out of 5 average rating, 136 reviews

Smith Rock Hideout - Cascade mountain views

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

Dec 24 – 31

G$30,317 GYD per night