Holiday rentals in Sisters

4.98 out of 5 average rating, 125 reviews

Cozy Mountain Escape: Amazing Views! Hot tub!

Relax in this calm, stylish newer home! The unobstructed mountain views are Jaw-dropping!! Walking distance to all that this amazing town has to offer. Enjoy the mountains and wildlife from the upper and lower decks after a day of exploring. Located in the desirable Pine Meadow Village neighborhood. Includes access to clubhouse, with a seasonal pool and a hot tub. You will take part of the mountain escape experience with you, wherever you go, and the memories you create will last a lifetime!

4.94 out of 5 average rating, 125 reviews

Apartment in Sisters

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

4.99 out of 5 average rating, 501 reviews

Cabin in Bend

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.

4.98 out of 5 average rating, 281 reviews

Home in Terrebonne

Pointe of Blessing with hot tub and canyon views

We hope you will enjoy our Pointe of Blessing. We feel our canyon perch is a gift from God-just 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. Prepare to relax unwind and enjoy spectacular sunrises and moonrises.

4.99 out of 5 average rating, 116 reviews

Apartment in Sisters

Beautiful Sisters Condo - Great location

Great location! Recently renovated this 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The sauna and hot tub are open year round. There is a club house that 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 area.

4.99 out of 5 average rating, 247 reviews

Home in Terrebonne

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.

4.91 out of 5 average rating, 170 reviews

Cabin in Culver

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.

4.94 out of 5 average rating, 166 reviews

Flat in Sisters

Contemporary apartment in Sisters, OR. USA

A contemporary 2 bedroom apartment in a quiet neighborhood just 4 blocks from Sisters main street. Minutes from music venues, festival locations, trails, and popular biking routes. Sisters has art, music, movie theater, good coffee, beer, restaurants, and boutique shopping. Village Green is close by. Superb biking, hiking, skiing, fly fishing, and outdoor opportunities abound year round. The apartment is perfect for couples, solo adventurers, business travelers, and families.

4.92 out of 5 average rating, 146 reviews

Cabin in Sisters

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!

4.98 out of 5 average rating, 172 reviews

Guest suite in Sisters

Sunny Sisters Suite

Welcome to our spacious light filled 700 sq. ft. studio comfortably furnished with a private entrance from the deck. It is located on 5 acres in a quiet neighborhood just a couple minutes drive or bike to downtown Sisters. Deer and fawns are often on the property and can be seen early in the morning grazing in the yard and garden. The National Forest with trails for biking and hiking can be accessed a couple minutes walk down the road.

Superhost

4.92 out of 5 average rating, 125 reviews

Sisters Home Upper - One bedroom/One bath -

New and modern, bright and cheery, all you need for comfortable lodging with short walk to downtown with plenty of parking. If you plan to be out and about most of the time you are visiting Sisters, this place is perfect and comfortable for up to 5 people. Park the car, close to everything in Sisters! Walk to town for coffee, dinner, and shopping. This is one of two suites available, also available Sisters Home Lower Two dog max.

4.85 out of 5 average rating, 165 reviews

Downtown Sisters - Juniper Building

This beautiful home in the heart of Sisters gives you easy access to all Sisters has to offer. Gourmet coffee and pastries are right down the street, and pizza is right next door. Relax on the beautiful covered deck or take advantage of nearby hiking, rock climbing, ski resorts, and the vibrant Sisters art scene.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Sisters holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sisters

5 out of 5 average rating, 11 reviews

Cabin in Sisters

Cabin Retreat @ Black Butte Ranch Hottub

JordanRating, 5 stars2 weeks ago

We were at Black Butte Ranch for a wedding. The cabin was perfect for our stay. Very clean, host gave good instructions and was proactive with information, and it had all the amenities we would need. Would stay again.

5 out of 5 average rating, 4 reviews

Beautiful Townhome with Patio

ShawnRating, 5 stars1 week ago

I've stayed in many vacation rentals over the last forty years, and this home is one of the nicest I've been in. It is cozy, yet roomy, with beautiful artwork throughout the house. The furniture is very comfortable and we slept well in the beds. We didn't use the BBQ grill but we enjoyed sitting out on the comfortable patio chairs. The clubhouse, pool and hot tub are practically in the back yard, across a sweet little creek with a bridge. The location is convenient being walking distance to downtown's cute shops, galleries, restaurants, bike rentals, and coffee. The neighborhood streets are safe for kids' bike riding or scootering, and if you walk a few blocks west, there are great views of the mountains (don't forget your camera/phone). Marcie is a great host who answered our questions almost immediately every time. I'm already checking for open dates later this year.

4.75 out of 5 average rating, 4 reviews

Cozy Cabin in Tollgate

LaceyRating, 5 stars1 week ago

This house is worth the stay. It not only has a hot tub, but you have access to the community pool. There are a lot of places to walk and bike to enjoy nature, but it is a 5 minute drive to downtown Sisters, so you are close! We appreciated a place to retreat too when we weren’t out and about. It’s truly peaceful. We will definitely book this again on our next Sisters vacation.

4.87 out of 5 average rating, 371 reviews

Townhouse in Sisters

Walk to Town Family Meeting Place AIRBNBOB

ScottRating, 5 stars1 week ago

Nice area close to town. Would definitely stay again!

5 out of 5 average rating, 9 reviews

Oregon Retreat for 12 – Hot Tub & Mountain Views!

MishaRating, 5 stars1 week ago

The home was spectacular! Tons of space, storage, and outdoor areas for relaxing. Everything you need for a home base in Sisters, this place has and more. Highly recommend!

4.94 out of 5 average rating, 33 reviews

Cabin in Sisters

Clover Cabin

ChristyRating, 5 starstoday

The cabin was just perfect - had everything we needed, was comfortable, incredibly peaceful and beautiful setting. Scott was quick to respond to a question for a local recommendation. We were lucky enough to be greeted by their dogs on our second day, which led to an impromptu and lovely conversation with Scott and Sarah. Lovely place and lovely hosts.