House vacation rentals in Sisters

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!

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!

4.84 out of 5 average rating, 655 reviews

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.

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.

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, 259 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, 328 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.

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, 304 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.

4.78 out of 5 average rating, 429 reviews

A wooden sign displaying 'Fall Creek' is mounted on the exterior wall of the suite, featuring a blend of red and blue colors. Two black sconces are positioned beside the sign, and a glimpse of the patio area is visible through the nearby glass door.

Home in River West

Fall Creek Suite - Awesome Westside Location

The Fall Creek suite is a great home base for adventurers of all kinds. The central-NW location offers easy access to great restaurants, shops, and trendy hangouts, while also being situated perfectly for exploring Central Oregon's awesome outdoor offerings like Mt. Bachelor, the Cascade Lakes, Smith Rock, and our beautiful natural rivers. Families, groups, and solo travelers alike will love the simple, single level layout. The suite also offers a patio area, along with a secure garage.

4.87 out of 5 average rating, 459 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.

4.93 out of 5 average rating, 239 reviews

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.

Home in Redmond

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.

A spacious living area is defined by a large sectional couch and a wooden coffee table. The adjacent dining space features a table with four chairs. Natural light enters through the glass doors leading to the outdoor area, complemented by neutral-colored walls and modern kitchen cabinetry.

4.83 out of 5 average rating, 195 reviews

Walk to Downtown Sisters - DOG Friendly - Updated!

This beautiful, modern, and family-friendly home is located right in the heart of Sisters and is just a 2 minute walk from all the shops, restaurants, and events that downtown has to offer. Not only will you love this home, but your furry friend and children will be pleased with the spacious fenced-in front yard and large park right across the street. We take pride in the cleanliness, spaciousness, and extra amenities that are offered to ensure the perfect Sisters get-away.

4.95 out of 5 average rating, 121 reviews

Home in Orchard District

Remodeled Gem of Midtown

Welcome to our home in Bend, OR! Our cozy, newly renovated midcentury modern home is centrally located in charming Midtown Bend. Enjoy a bonfire in the backyard, or relax after a day on the mountain in the elevated living area. Take a stroll with your pup down to Hollinshead Park to enjoy the trees and beauty of the neighborhoods. We are conveniently located: 5 Minutes to Downtown Bend 7 Minutes to Old Mill District 35 Minutes to Mt. Bachelor

Popular amenities for Sisters house rentals

Kitchen

Wifi

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

4.8 out of 5 average rating, 186 reviews

The single-story home features a natural wood exterior surrounded by tall trees. A spacious front deck includes a dining table with an umbrella and two chairs, providing a welcoming outdoor seating area. The driveway leads to a two-car garage.

Home in Sunriver

Sunriver Home; Hot Tub, SHARC, Fireplace and More!

A two-story home situated among tall pine trees, featuring a warm, neutral exterior. The driveway leads to a wooden staircase that connects to the front entrance. The surrounding landscape is covered in soft pine needles and natural earth tones.

4.94 out of 5 average rating, 100 reviews

Large Black Butte Home With Private Hot Tub

An illuminated hot tub with turquoise water sits in the foreground, surrounded by trees. Warm string lights hang above, casting a soft glow over the outdoor seating area, which includes two chairs and a table, creating a cozy atmosphere for relaxation.

4.94 out of 5 average rating, 109 reviews

XL Hot Tub, Dog Friendly, EV Charger, Fenced Yard

4.92 out of 5 average rating, 178 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

A modern home is surrounded by snow-covered trees, showcasing large windows that reflect natural light. The wooden exterior complements the winter landscape, while steps lead from the porch to the yard blanketed in fresh snow.

4.92 out of 5 average rating, 131 reviews

Black Butte Ranch Home with THE View

A cozy living space features a comfortable gray sofa with decorative pillows, a wooden coffee table, and a dining area with a table and chairs. Natural light fills the room through tall windows, illuminating the rustic wooden accents and equipped kitchen in the background.

4.73 out of 5 average rating, 140 reviews

Tollgate Cabin in the Pines (with Level 2 Charger)

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.

4.94 out of 5 average rating, 132 reviews

Black Butte Ranch Family Friendly Home Sleeps 14

Weekly house rentals

4.91 out of 5 average rating, 194 reviews

The RiverBend House - near Sunriver & Mt Bachelor

Home in Black Butte Ranch

A spacious living area features large windows that frame views of the surrounding nature. Comfortable seating includes a leather sofa and plush chairs, while a stacked stone fireplace adds a cozy touch. Sliding doors open to an outdoor patio, enhancing the connection with the outdoors.

5 out of 5 average rating, 40 reviews

Black Butte Ranch Cabin on the 7th Fairway

A classic two-story home is presented against a vibrant sunset sky. The wrap-around porch features white columns and is surrounded by neatly trimmed shrubs. Large windows face the yard, allowing for ample natural light to enter the living space.

4.97 out of 5 average rating, 97 reviews

Downtown Pine Mountain Paradise

4.98 out of 5 average rating, 306 reviews

Home in Orchard District

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

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

4.95 out of 5 average rating, 674 reviews

A single-story home is framed by tall trees in a natural setting. The entrance is approached by a set of steps leading to a small porch. Large windows allow for natural light, while the surrounding area features a grassy landscape.

Home in La Pine

Cozy Getaway in the Pines

5 out of 5 average rating, 22 reviews

Beautiful Townhome with Patio

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, 319 reviews

"Urban Spruce" - Great peaceful location!!

Private house rentals

4.89 out of 5 average rating, 55 reviews

Beautiful Downtown Sisters Home- Spacious 1 Level

An outdoor space showcases a manicured green lawn with a spacious patio area. Stylish seating arrangements and a dining table are visible, accompanied by outdoor heating elements. The home's expansive windows offer a glimpse into the interior, illuminated by soft lighting, framed by trees and a colorful sky.

4.97 out of 5 average rating, 34 reviews

New! Luxury Home ~River View/Access~Hot Tub

4.93 out of 5 average rating, 40 reviews

Home in Larkspur

Private apartment in home

A bright living area features large windows offering expansive views of the surrounding mountains and landscape. A dark sectional sofa is complemented by decorative pillows. A circular coffee table is centered on a textured rug, enhancing the inviting atmosphere of the space.

4.98 out of 5 average rating, 45 reviews

Mountain View Home in Tumalo - 7 day minimum

A charming two-story home is framed by greenery, featuring a mix of wooden and stone accents. The front porch is sheltered under a gabled roof, with a decorative wooden lattice supports. A wooden fence surrounds the property, enhancing the peaceful residential feel.

5 out of 5 average rating, 51 reviews

Charming 3BR 2.5B Retreat in the Heart of Sisters

The living area features a spacious layout with a large sectional sofa and multiple armchairs. Natural light filters through the windows, illuminating the warm wood floors. A wood stove adds to the cozy atmosphere, while a large TV is mounted on the wall for entertainment.

5 out of 5 average rating, 75 reviews

Quiet Relaxing Home Near Sunriver Hot Tub Bikes

A spacious living area features large windows providing natural light and a view of the surrounding trees. A comfortable sofa and coffee table are arranged around a fireplace, while a flat-screen TV is positioned nearby. A dining table is visible in the background.

4.95 out of 5 average rating, 22 reviews

Great deals next summer during deck construction.

A spacious seating area is highlighted by a rich wooden A-frame design, with large windows allowing natural light to fill the space. A cozy wood stove is positioned against a stone wall, while a plush side sofa complements the warm tones of the interior.