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
An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.
Bungalow in Bend
5 out of 5 average rating, 108 reviews

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally-located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding and pillows, dedicated free parking (incl. extra cars or small RV), outdoor dining and patio area, washer/dryer, and kitchen fully stocked with everything you need for fun and relaxation for all seasons!

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, 938 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!

Top Guest favourite
A spacious living area features a sectional sofa in neutral tones, accompanied by a soft area rug. A stone fireplace adds warmth, while large glass doors open to a private balcony with outdoor seating. Natural light fills the room, enhancing the inviting ambiance.
Condo in Sisters
4.99 out of 5 average rating, 132 reviews

Beautiful Sisters Condo - Great location

Great location! Remodeled 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The hot tub/sauna are open year round. The club house includes ping pong, foosball and a pool table. You just need to walk through the city park and across the creek to get into town. We are also located a block or two from the MovieHouse and Three Creeks Brewing. Enjoy bike paths close by and lots of hiking in the area. Easy self check-in and out.

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, 531 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 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, 333 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, 226 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
4.9 out of 5 average rating, 230 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.

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
4.93 out of 5 average rating, 178 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!

Guest favourite
A cozy living area is seen, featuring a dark sofa against the wall, a coffee table, and a flat-screen TV mounted nearby. The kitchenette includes dark cabinetry, a microwave, and a mini fridge. A clock on the wall and ample natural light enhance the space.
Townhouse in Sisters
4.87 out of 5 average rating, 404 reviews

Walk to Town Family Meeting Place AIRBNBOB

Home built in 2017 with AirBnb in mind. Private entrance. Smart lock access to upstairs flat. Master bedroom with king bed. Balcony bedroom with amazing queen electric bed (New). Trundle couch with two single beds. Electric cooking area. Mini fridge. Balcony view of snowcapped mountains. High speed WIFI. Wide Screen TV. Apple TV access to Netflix, Youtube, Amazon Prime, etc. New Bidet installed in April 2019.

Popular amenities for Sisters holiday rentals

When is the best time to visit Sisters?

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Avg. price$287 NZD$291 NZD$294 NZD$279 NZD$312 NZD$390 NZD$407 NZD$372 NZD$332 NZD$293 NZD$282 NZD$298 NZD
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Frequently Asked Questions

  • What are the best places to stay in Sisters?

    Sisters has cozy vacation rentals, cabins tucked among pine trees, and homes near downtown for easy access to shops and dining. Nearby neighborhoods around Barclay Park and the historic center are frequently suggested for their relaxed atmosphere.

  • What are the best things to do in Sisters with kids?

    Families often explore local parks, visit the children's section at Sisters Library, or discover engaging exhibits at the nearby museum. Outdoor adventures, such as kid-friendly hikes and nature walks, are easy to find around the town.

  • What are some of the best things to do in Sisters?

    Explore the Sisters Historic District, browse locally owned shops, or check out art galleries highlighting regional creativity. Outdoor enthusiasts can discover forest trails, scenic picnic spots, and mountain views just outside town.

  • How is the weather in Sisters?

    Sisters has cold winters with temperatures from 23–44°F (-5–7°C) and light to moderate snowfall, while summers are warm and dry, often reaching 88°F (31°C). Spring and autumn bring mild days and cooler nights, so layering is helpful.

  • When is the best time to visit Sisters?

    Late spring through early fall is often recommended for clear, warm weather and outdoor festivals, with summer highs near 88°F (31°C). Winter brings snow, inviting visitors interested in seasonal mountain activities and quieter trails.

  • What are the best places to visit in Sisters?

    Frequent recommendations include the Sisters Historic District for its local heritage, art galleries, and Barclay Park's gathering space. The area has vibrant shops and scenic viewpoints around town.

  • What are some hiking trails in Sisters?

    Sisters has access to forested trails such as the Peterson Ridge Trail, portions of the Metolius-Windigo Trail, and wildflower paths near Whychus Creek. High desert landscapes and mountain views are a regular part of the experience.

  • What are some family activities we can do in Sisters?

    Families can explore parks for picnics, visit Sisters Library for story time, or enjoy local ice cream shops. Outdoor spaces often have play areas and easy walking paths for all ages.

  • What are some of the best day trip ideas from Sisters?

    Plan a visit to local lakes for paddling, discover waterfalls along nearby scenic routes, or explore lava fields with marked trails. Regional museums and artists' studios provide a different take on High Desert culture.

  • Are there any pet friendly accommodations available in Sisters?

    Many vacation rentals in Sisters welcome pets, especially those near forest edges or local parks. Walking trails and dog-friendly outdoor spaces make it easy to travel with animal companions.

  • What are some local tips for visiting Sisters?

    Locals suggest picking up picnic supplies at the farmers market, packing layers for temperature swings, and exploring the side streets for quieter cafes. Check community boards for seasonal art shows and outdoor markets.

  • What is Sisters known for?

    Sisters is known for its mountain views, small-town Western character, and annual quilting gatherings. The community has a strong outdoor recreation tradition and a lively arts scene.

  • What are the best hidden gems to explore in Sisters?

    Seek out local art studios tucked along quieter streets, taste handmade treats at small bakeries, or enjoy sunrise at nearby viewpoints. Less-traveled nature trails often lead to peaceful forest or creek settings.

  • What are the best foods to try in Sisters?

    Home-baked pastries, locally roasted coffee, and regional specialties like elk or trout are frequently suggested. Outdoor food stands and seasonal farmers markets highlight fresh produce and handcrafted snacks.

  • What should I bring for a trip to Sisters?

    Pack layers for cool mornings and warm afternoons, comfortable walking shoes for uneven paths, and a reusable water bottle. Sun protection and a rain jacket can help with the area's shifting weather.

  • What is the nightlife in Sisters like?

    Nightlife in Sisters is relaxed, with live music at local venues, casual bars, and cozy cafes. Some evenings feature open mic nights or performances highlighting area musicians.

  • What are the most popular events or festivals in Sisters?

    The Sisters Rodeo in early summer, the Sisters Outdoor Quilt Show in July, and music festivals throughout the year are among the most popular annual gatherings. Local art walks and artisan markets are also frequently suggested.

  • Are there family friendly vacation rentals in Sisters?

    Sisters has a variety of family-friendly vacation rentals, including cabins and homes with outdoor spaces or nearby playgrounds. Many hosts provide amenities tailored to travelers with children.

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!

  1. Airbnb
  2. United States
  3. Oregon
  4. Deschutes County
  5. Sisters