Holiday houses in Sisters

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Top-rated holiday rentals in Sisters

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.98 out of 5 average rating, 934 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!

Guest favourite
A newly built condo complex features a charming entrance with front porches. Well-maintained landscaping includes colorful flower beds and green shrubs, framed by tall trees. The clear blue sky above casts a bright ambiance, accentuating the inviting architectural design.
Condo in Sisters
4.92 out of 5 average rating, 144 reviews

Views! 1 Blk to Town,New+Spotless, pets ok- Middle

Prime Sister's location, Safe upscale neighborhood! Newly built condo offers EVERYTHING you expect without sacrificing a thing! Only 1 block to downtown restaurants/shopping. Leave your car at the unit and walk! Fully stocked Kitchen, comfy king size bed in master, queen size sofa / sleeper in living room! Relax on sofa or the new recliner, excellent wi-if, internet, cable tv, Netflix. Washer/dryer to use too! Pet friendly, under 40 lbs, $35.00 pet fee per pet. This unit is also ADA co

Top Guest favourite
A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.
Cabin in Bend
4.99 out of 5 average rating, 529 reviews

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

Top Guest favourite
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
4.97 out of 5 average rating, 543 reviews

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

Top Guest favourite
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.
Home in Terrebonne
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.

Guest favourite
A welcoming living area features a gas fireplace set within a brick surround. Large windows provide natural light and views of the outdoor space. A comfortable seating arrangement includes a dark sofa and a coffee table, while a bookshelf is filled with various books.
Townhouse in Sisters
4.89 out of 5 average rating, 227 reviews

Sisters Getaway

Welcome to Sisters! This 2 bedroom, 2 bath condo is situated in the Pine Meadows development & 7 min walk to downtown Sisters. Sunny corner unit on main flr. Open-concept living w/ 9ft ceilings, gas fireplace & recently remodeled w/ new appliances. Amazing primary suite w/walk-in closet & private deck Downtown Sisters has restaurants, antiques, bike shops & Sisters Coffee Shop. Pool, hot tub, tennis courts, & sculpted walking path offer views of the magnificent 3 Sisters mountain range.

Top Guest favourite
An open-plan living space features a wooden dining table surrounded by white chairs, complemented by a decorative plant in a pot. Natural light filters through a skylight and windows, enhancing the wooden beams and soft color palette of the room.
Cabin in Sisters
5 out of 5 average rating, 154 reviews

Modern Mountain Cabin Close to Town (HOT TUB!)

Come enjoy this beautiful home filled with tons of natural light, skylights, a cozy fireplace and a highly functional open floor plan. The backyard features a newly built deck and outdoor dining, BBQ, patio loungers, fire pit and HOT TUB! All the benefits of a quiet neighborhood while being just a 5 - 10 minute walk from the heart of downtown Sisters and a short drive to endless hikes and running trails, beautiful lakes and rivers, skiing, rock climbing, mountain biking and so much more.

Superhost
A colorful hammock is suspended from a snow-covered tree, inviting relaxation. The quaint WeeHouse, featuring large windows and a bright yellow door, is partly obscured by the snow. A serene winter landscape surrounds the property, showcasing the tranquility of the setting.
Tiny home in Bend
4.84 out of 5 average rating, 243 reviews

IT'S A WEE HOUSE

Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

Guest favourite
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
4.89 out of 5 average rating, 227 reviews

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.

Top Guest favourite
A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.
Condo in Bend
4.97 out of 5 average rating, 275 reviews

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

Guest favourite
The exterior of a charming A-Frame cabin is surrounded by tall trees and features a welcoming front porch. A rustic concrete dining table and red Adirondack chairs are positioned on a gravel patio, offering a comfortable spot for outdoor relaxation.
Cabin in Sisters
4.92 out of 5 average rating, 173 reviews

A-Frame Cabin on 4.5 Acres - HOT TUB, Dog Friendly

This 2 bedroom Northwest themed A-Frame is the perfect destination for your couples retreat or small family vacation! It is situated on a super peaceful 4.5 acre lot and is only a 7 minute drive to Downtown Sisters. Our cabin sleeps 4 people comfortably in the 2 upstairs bedrooms, has 2 full bathrooms, a stocked kitchen, and a private back patio featuring our brand new hot tub. This is a dog friendly home so you are more than welcome to let your furry friend tag along!

Top Guest favourite
Cabin in Bend
4.93 out of 5 average rating, 187 reviews

Eco cabin near Bend: sauna, hot tub, EV plug

Location Highlights • Peaceful acre in Three Rivers • 30 min to Bend and Mt. Bachelor • 15 min to Sunriver Relax • Soak in the hot tub under the stars • Rejuvenate in the barrel sauna • Unwind by the fire pit • Drift off in a hammock with your favorite book Inside • Warm knotty pine walls and juniper accents • Full kitchen, WiFi, 2 baths • Eco-conscious with bio-based flooring Book now and kickstart your Central Oregon adventure!

Popular amenities for Sisters holiday rentals

When is the best time to visit Sisters?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$288 NZD$291 NZD$294 NZD$279 NZD$312 NZD$390 NZD$407 NZD$372 NZD$333 NZD$293 NZD$282 NZD$298 NZD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Sisters?

    Yes! Work meets play with ease at over 40 vacation rentals in Sisters featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Sisters?

    Four-legged friends are welcome in Sisters. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there Sisters vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Sisters, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Sisters?

    Sisters has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in boutique hotel rentals in Sisters?

    Experience the best of Sisters with our boutique hotel rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Sisters have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Sisters. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Sisters have wifi?

    Absolutely! We offer over 10 townhouse rentals with wifi in Sisters. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Sisters have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Sisters. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Sisters

  • Total holiday rentals

    Explore 140 holiday rentals in Sisters

  • Nightly prices starting at

    Sisters holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 8,390 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Sisters holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Sisters rentals

  • 4.9 Average rating

    Sisters stays are highly rated by guests—averaging 4.9 out of 5!

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