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, 284 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.

Top guest favourite
The exterior of a rustic A-frame cabin features wooden siding and a sloped roof, surrounded by tall Ponderosa trees. A spacious porch with outdoor furniture invites relaxation, while double French doors provide access to the living area. Distinctive architectural details enhance the cabin's charm.
Cabin in Bend
4.93 out of 5 average rating, 365 reviews

Quaint A-Frame Cabin close to Mt Bachelor

Cosy two story A-Frame cabin among Ponderosa trees in a quiet residential. 5 minutes drive to Sunriver Village, 16 min. Mt Bachelor, 20 m Bend downtown. Living room has a comfy sectional, a single reclining armchair and TV. My cabin has a well appointed kitchen, laundry room with W/D, a Bathroom/Shower downstairs. A 2 bedrooms upstairs with Queen size bed. There is a powder room/toilet upstairs in the hallway. NO SMOKING/NO PARTIES /4 MAX .Please leave my home how you found it. Thank you 😄

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
4.93 out of 5 average rating, 147 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, 537 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 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
4.84 out of 5 average rating, 666 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.

Top guest favourite
A bright room is illuminated by large windows with dark blinds. It features a spacious bed, a small table with two chairs, and a kitchenette area. A mini-fridge and microwave are visible, along with a lamp and a side table.
Guest suite in Orchard District
4.92 out of 5 average rating, 406 reviews

Midtown Getaway- Private entrance and bathroom!

Just over 2 miles from downtown. This is a private room attached to our house with a separate entrance. The room has a double bed, full private bathroom, closet space, a kitchenette, and seasonal access to the outside deck and hammock. Includes heating and cooling controls, a mini-fridge/freezer, microwave, coffee maker, cups, plates, and utensils. Coffee, tea, snacks, ice provided. Great for late night arrivals or early departures! The space is quaint- room & bathroom- 185 sq. ft. total

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.

Top guest favourite
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.
Home in Terrebonne
4.99 out of 5 average rating, 325 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.

Guest favourite
The cabin features a welcoming entrance with a wood deck and rustic details. Framed by green trees, the two-story structure showcases a steep gabled roof and large windows, providing a warm and inviting sight. A path leads to the entrance, surrounded by low shrubs.
Cabin in Sisters
4.96 out of 5 average rating, 149 reviews

Pet + kid friendly w/ private hot tub!

Relax with the whole family at this peaceful cabin in Sisters! Take a short drive into downtown Sisters or ride bikes into town via neighborhood trails to do some shopping or explore the nearby lakes, rivers and mountains. Or stay in! Enjoy happy hour on the roof top deck, unwind in the steamy hot tub, cook dinner in the fully equipped kitchen, or have a BBQ on the outdoor patio! This is the perfect place to experience all Sisters has to offer! Just the getaway you've been waiting for!

Top guest favourite
Home in Sisters
4.93 out of 5 average rating, 129 reviews

Modern Tollgate Home - HOT TUB | Half Acre Lot

This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you stay at this Tollgate home you get all of the community amenities with it: community pool, pickle-ball/tennis courts, walking trails, basketball courts, etc. Bring the whole family as we comfortably sleep 6 people and enjoy the hot tub! This is an incredibly well-done high-end modern home that is virtually brand new. We are also a dog friendly home ($100/stay fee).

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, 249 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 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, 407 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$211 SGD$214 SGD$216 SGD$205 SGD$229 SGD$286 SGD$299 SGD$274 SGD$244 SGD$215 SGD$207 SGD$219 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 130 holiday rentals in Sisters

  • Nightly prices starting at

    Sisters holiday rentals start at $89 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 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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