Holiday rentals 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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Guest favourite
An open living space is visible, featuring a comfortable black couch with a plaid throw. A modern kitchen area with stainless steel appliances is seen, along with a dining table in the background. Warm wood flooring enhances the inviting ambiance.
Guest house in Terrebonne
4.87 out of 5 average rating, 280 reviews

Near SmithRock pets ok private heated bungalow

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

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.
Apartment in Sisters
4.92 out of 5 average rating, 145 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 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.
Flat in Redmond
4.97 out of 5 average rating, 545 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, 334 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.

Top guest favourite
A cozy sleeping area is presented, featuring a king bed adorned with a floral-patterned blanket in warm tones. A circular mirror and artwork above the bed add visual interest. A bedside table holds a soft lamp and a small plant, while natural light filters in from the window.
Guest suite in River West
4.99 out of 5 average rating, 496 reviews

Hillside Haven: Tranquil NW Studio Near the River

Wake up refreshed in this bright sanctuary overlooking a rocky hillside and grassy meadow in an historic neighborhood. Comfy king bed, private entrance, kitchenette, private bath & dedicated workspace. Walk to beautiful First Street Rapids Park footbridge (less than 1 min) & Downtown along the River Trail passing several parks. This unique space has charm along with an ideal location. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.♥︎

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, 244 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"

Top guest favourite
The RV interior features a spacious living area with a large sectional sofa and a central kitchen island. Modern appliances, including a stovetop and refrigerator, are visible, along with ample cabinetry. Windows provide natural light, framed by simple curtains, and a soft area rug adds comfort.
Campervan/Motorhome in Bend
4.97 out of 5 average rating, 178 reviews

Glamping! Quad Slide RV on a Tumalo Hobby Farm

Welcome to the Tumalo hobby farm! Here you will have your own 42ft 2019 Forest River RV, located on our lovely Tumalo property. Nestled in the midst of goats and chickens, this will be a perfect landing for work or play. Enjoy the mountain views and bright stars after your day out adventuring around Central Oregon. Within close driving distance to Bend, Sisters, Redmond, Mt Bachelor and Hoodoo. This RV is fully hooked up with power, water, heat, A/C, internet, and is ready for you.

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.

Top guest favourite
A cozy bedroom features a spacious bed with a colorful blanket, complemented by wooden accent walls. A wall-mounted flat-screen TV is above a modern electric fireplace. A small table with two chairs is positioned nearby, with a mirror framed in green accentuating the space.
Guest suite in Bend
5 out of 5 average rating, 117 reviews

Sixties Suite Spot

Escape to our cozy, retro suite, a serene haven centrally located near Pine Nursery Park. Enjoy a tranquil retreat with high-quality amenities, dog-friendly comforts, and snowboard/ski storage. With a semi-private yard featuring Adirondack chairs, easy parking, and a vibrant, photo-ready design, it's perfect for relaxation and adventure. We proudly welcome 2SLGBTQIA+ guests, offering a warm, inclusive environment. Discover a blend of charm and convenience at our unique getaway!

Top guest favourite
A cozy living area features a dark sofa with bright pillows, complemented by a colorful area rug. The kitchen is visibly modern, showcasing stainless steel appliances and a light blue accent wall. Natural light filters in through the skylight and window.
Flat in Larkspur
4.96 out of 5 average rating, 381 reviews

Larkspur Garden Guesthouse

Located in Bend's Midtown and with access to the Larkspur trail that leads to iconic Pilot Butte, this bright, newly built 450 sq. foot apartment balances cozy and modern elements to make your stay in Bend comfortable. Equipped with a full kitchen, a separate room with a queen bed, a deep, relaxing tub, a sofa that converts into a memory foam queen bed, a TV with access to Netflix, and a separate laundry room. Our space is a great option for 2 guests, but it can fit up to 4.

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$213 SGD$216 SGD$218 SGD$207 SGD$231 SGD$289 SGD$302 SGD$276 SGD$247 SGD$217 SGD$209 SGD$221 SGD
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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 $64 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    130 of Sisters holiday rentals include wifi 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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