Cottage vacation rentals in Sisters

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Popular amenities for Sisters cottage rentals

Cottage rentals with a hot tub

Top guest favorite
The home’s exterior features a welcoming entrance with a front porch, surrounded by shaded trees and lush greenery. A gravel pathway leads to the front door, flanked by large windows that allow natural light to enter the space.
Cottage in Bend
4.94 out of 5 average rating, 79 reviews

Cozy 3 bedroom house, hot tub, near Sun River

JasonRating, 5 stars9 months ago
We had a fantastic stay at Talia's place near Sunriver! The home was cozy and clean and had everything we needed for a relaxing getaway. The location was perfect—close to all the outdoor activities we love, yet tucked away in a quiet, peaceful setting. Talia was a fantastic host, quick to respond, and very accommodating. We couldn't have asked for a better experience and look forward to returning soon!
Guest favorite
A charming cottage exterior is presented, featuring a welcoming front porch with red chairs and decorative throw pillows. Flower beds, filled with white and purple blooms, line the path leading to the entrance. Three vertically positioned windows above the door allow natural light to enhance the facade.
Cottage in Sisters
4.95 out of 5 average rating, 41 reviews

TruNorthwest Retreat | Walk to Town • Pool • Dogs

AnnieRating, 5 stars6 days ago
Great location and space in sisters! As described!
Guest favorite
A spacious patio area is presented with a large red umbrella over a dining set featuring four patterned chairs. A hot tub is positioned nearby, with a grill partially visible in the background. Surrounding greenery adds a touch of nature to the setting.
Cottage in Bend
4.93 out of 5 average rating, 288 reviews

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

RitaRating, 5 stars2 weeks ago
Great location and a very comfortable home, just as described. The back deck and hot tub were a bonus. Since the location is close to downtown, the river, and the old mill district, the bikes came in very handy. We'd stay again!
The exterior of the cottage is shown with a charming deck and two white chairs positioned under string lights. A well-maintained path leads through lush greenery and stone steps to the entrance, highlighting the inviting atmosphere of the cottage.
Cottage in Orchard District
4.89 out of 5 average rating, 308 reviews

The Blackberry Cottage

MollyRating, 5 stars3 weeks ago
We stayed for the Pole Pedal Paddle and had a great time here! Really enjoyed the hot tub and being so close to Pilot Butte. Tomi was helpful and responsive when we had a question about the WiFi. We would love to come back!
Guest favorite
A charming cottage is depicted with a sloped roof and inviting front porch. Adjoining chairs sit on a lush green lawn, surrounded by well-maintained shrubs and seasonal flowers. A stone pathway leads to the entrance, framing the structure in a serene outdoor setting.
Cottage in Sisters
4.96 out of 5 average rating, 27 reviews

Cottage Live/Play in the Heart of Downtown Sisters

KrystynaRating, 5 stars1 month ago
We had a wonderful stay in Sisters at David & Victoria’s place. Walkable to town, peaceful neighborhood, perfect view of the Sisters mountain range. Their place had plenty of space for us and the bed was comfortable.
Guest favorite
A modern kitchen features sleek cabinetry and quartz countertops, complemented by stainless steel appliances. Two wooden stools sit at the kitchen island, with a spacious layout that encourages cooking and socializing.
Cottage in Old Bend
4.96 out of 5 average rating, 260 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

JudyRating, 5 stars2 weeks ago
I have rented many Vacation rentals in the USA and Mexico . I would rate this as the best yet! You can walk everywhere, we walked to the concert to the river and out to eat. The restaurant recommendations were all outstanding. Erin was very responsive and friendly. The cottage was beyond well stocked with everything. We did plan to bring our dogs but they ended up staying home but the yard would be perfect for them. Last but not least all the neighbors were so friendly!
Top guest favorite
A cozy home is nestled among tall trees, featuring a spacious deck that wraps around the front. The structure is painted in a soft shade of yellow, highlighted by a chimney, and surrounded by natural landscaping and shrubs.
Cottage in Bend
5 out of 5 average rating, 38 reviews

Cloudchaser Cottage: Cozy Get-Away

Sarah Rating, 5 stars2 months ago
We loved this property. It was in a great area and we loved the neighborhood. The house was well equipped and very peaceful and great floor plan. The just was so helpful and responsive. Would recommend and will rent again.
Top guest favorite
An outdoor seating area is surrounded by snow-covered ground, featuring a rectangular fire pit at the center. Several chairs with cushions in various colors are arranged around it. The cottage's warm lights glow invitingly through large glass doors, framed by tall trees in the background.
Cottage in Sisters
5 out of 5 average rating, 16 reviews

Hot Tub, Fire Pit, Dog Friendly

AshleyRating, 5 stars1 week ago
We had a great stay! House was very clean and Kenny was a great host

Pet-friendly cottage rentals

Guest favorite
A cozy living area is presented, featuring a blue couch and two brown chairs. A wooden dining table is visible, surrounded by wooden chairs. Warm lighting is created by pendant lamps above the table, complemented by a table lamp on a side table. A door leads to the outside.
Cottage in Old Bend
4.92 out of 5 average rating, 130 reviews

2 Bedroom Delight In The Old Mill

AshleyRating, 5 stars2 weeks ago
Amazing place to stay in Bend. Walked or took the cruiser bikes everywhere. Headed to a concert at the ampitheatre, toodled along the river, and explored downtown -- all just 8-10 minutes away. Had a great stay!
Guest favorite
A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.
Cottage in Redmond
4.89 out of 5 average rating, 72 reviews

Blossom Cottage Studio

LorettaRating, 5 stars3 weeks ago
Great place to stay for a quick overnight trip
Guest favorite
A light-filled living room features a gray sofa with a minimalist coffee table in front. A woven pouf adds texture to the space, while a floor lamp provides ambient lighting. A spiral staircase leads to an upper level, enhancing the room's vertical design.
Cottage in Bend
4.92 out of 5 average rating, 163 reviews

Amazing Location! | Charming, Cozy Cottage

JohnRating, 5 stars10 months ago
Great little house with a lovely backyard and walkable to tons of good spots in Bend. Hope we can come back in the winter and stay again!
Guest favorite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne
4.89 out of 5 average rating, 300 reviews

Quiet central Oregon desert retreat with a view!

CharlesRating, 5 stars5 days ago
We stayed the last days in May and the first days in June 2025. The place was clean with everything needed to relax, enjoy our stay and also do our own cooking. We sat outside at sunset and watched the stars come out. We hiked at Smith Rock State Park and visited Bend and Redmond. It was a great stay and I'm recommended it to friends and hope to be back next year.
Guest favorite
The exterior of the Greeley Cottage features a charming white facade with dark trim. Multiple windows offer natural light, while potted plants flank the entrance. A black front door is adorned with a decorative lamp, inviting guests into the home.
Cottage in Bend
5 out of 5 average rating, 11 reviews

Greeley Cottage: Steps to downtown Bend

JamesRating, 5 stars3 weeks ago
We had a great stay. The place is spacious - separate living room, kitchen with dining area, two bedrooms, separate bathroom. It's great that way. And all clean and tastefully appointed. The location is a mix of slightly funky (it's basically located on an alley) and wonderful - you are a block or two from downtown Bend. It's a great combo, actually. We really enjoyed it.
Guest favorite
An outdoor patio area is surrounded by a wooden fence, featuring a round black table with four chairs, a vibrant red umbrella, and a coffee table. Colorful flowers and greenery are planted along the edges, creating a serene outdoor space.
Cottage in Bend
4.87 out of 5 average rating, 141 reviews

Guest Favorite! Prime West Side Location, Hot Tub

SarahRating, 5 stars4 weeks ago
Erin’s place was perfectly located and super cozy. We didn’t spend as much time there as I hope we can in the future but it was exactly what we needed and we appreciated that. Erin is very easy to communicate with and she navigates problem solving with ease . We hope to stay again and enjoy the amenities!
A rustic log cabin is seen nestled among tall trees, featuring green-framed windows. A circular fire pit with a bright flame is surrounded by stones, and wooden picnic tables are positioned nearby, offering a communal space for relaxation amid nature.
Cottage in Crescent
4.79 out of 5 average rating, 24 reviews

Deschutes 2 Bedroom Cabin

MeganRating, 5 stars3 months ago
Stunning lake view from beautiful picture window. Watched a brilliant sunrise, ducks and an eagle from the window. The kids found a sweet little sledding hill that was the perfect size for them, made snowmen and had snowball fights. Beds were comfortable and cabin was warm. Kitchen was missing lids for the pots and basic staples. The general store was open. Would definitely visit again!
Top guest favorite
A comfortable living area features warm brown leather sofas adorned with decorative pillows. A small ottoman is centered in the seating arrangement. Natural light filters through sheer curtains, and a flat-screen TV is mounted on the wall, enhancing the inviting atmosphere.
Cottage in Prineville
4.95 out of 5 average rating, 62 reviews

Court St. Cottage | Downtown Prineville Getaway

ErinRating, 5 stars1 week ago
Great place to stay! The location was peefect, within walking distance to downtown, food trucks and parks. The house was amazing, it was cozy and had everything we needed. Super clean, and the host was super responsive.

Private cottage rentals

Top guest favorite
The exterior of the home is framed by lush greenery, showcasing a well-maintained lawn. A welcoming porch features steps leading up to the front door, flanked by a small seating area and flower pots, enhancing the inviting look of the rental.
Cottage in Bend
4.94 out of 5 average rating, 418 reviews

An Urban Base to Bend's Adventures!

KaitlinRating, 5 stars2 months ago
This place was amazing. It had everything I needed, was centrally located and incredibly clean
Top guest favorite
A tranquil outdoor fire pit area features five bright red Adirondack chairs arranged in a semicircle around a stone-lined fire pit. The yard overlooks a peaceful river, surrounded by grasses and trees, creating an inviting space for relaxation.
Cottage in Old Bend
4.99 out of 5 average rating, 114 reviews

Riverfront Cottage– Walkable Old Bend Stay

TiaRating, 5 stars3 weeks ago
We had the best weekend. Jacalyn was so kind, responsive and went above and beyond to ensure we had a great trip. We even used the house Kayak for the PPP race we were in town for. We will stay here again!!! ⭐️⭐️⭐️⭐️⭐️
Top guest favorite
An above-ground hot tub is situated in the private yard, surrounded by snow-blanketed ground. Steam gently rises from the bubbling water, creating a serene atmosphere. A wooden fence encloses the yard, providing privacy, while a storage shed is visible in the background.
Cottage in Bend
4.95 out of 5 average rating, 420 reviews

Vintage Pink Hot Tub✓ Walkable✓

DebiRating, 5 stars1 month ago
Quaint and quiet. Clean and great location. Met our expectations. Super friendly hosts and very responsive. Have already recommended to friends.
Guest favorite
Cottage in Bend
4.97 out of 5 average rating, 116 reviews

River Camp House

TonyaRating, 5 stars3 weeks ago
Daniel’s place was perfect for our stay in Bend. We had a wedding at Tetherow Resort, so it was super convenient for this and other activities throughout Bend. The house was so clean and well stocked with everything we needed (and then some). Check-out instructions were clear and not complicated at all. I highly recommend for a small family or girls weekend. Thank you!
Top guest favorite
A serene view of Whychus Creek meanders through a lush landscape, framed by vibrant green trees. Sunlight filters through the foliage, casting dappled shadows on the water's surface, creating a calm and inviting atmosphere in nature.
Cottage in Sisters
4.98 out of 5 average rating, 165 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

SandyRating, 5 stars1 week ago
Awesome location and easy house to stay in. Stocked kitchen with everything you'd forgotten made it a super easy vacation to handle. Our second time here and we'll be back again.
Guest favorite
A lush green landscape is depicted, showcasing a serene park area with vibrant trees and flowering bushes. A peaceful water body can be seen in the background, where people are engaged in recreational activities. Light filters through the foliage, enhancing the natural beauty.
Cottage in Old Bend
4.96 out of 5 average rating, 260 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

JudyRating, 5 stars2 weeks ago
I have rented many Vacation rentals in the USA and Mexico . I would rate this as the best yet! You can walk everywhere, we walked to the concert to the river and out to eat. The restaurant recommendations were all outstanding. Erin was very responsive and friendly. The cottage was beyond well stocked with everything. We did plan to bring our dogs but they ended up staying home but the yard would be perfect for them. Last but not least all the neighbors were so friendly!
Top guest favorite
A wide shot captures a snow-covered mountain, with gentle slopes blanketed in fresh powder. The surrounding forest is adorned with snow-laden trees, and a soft pastel sky marks the horizon. The scene conveys a serene winter landscape, perfect for outdoor enthusiasts.
Cottage in Bend
4.98 out of 5 average rating, 112 reviews

The Tumalo House

Npulone@Gmail.ComRating, 5 stars1 week ago
Adorable and spotless clean home right near the new and fun shopping and eating options in Tumalo. Central to Sisters and Bend or Redmond sights but so quiet and fun walkable community away from the traffic. For me it was also close to Bend Equine for my horses special treatment. I loved working here, walking to delicious coffee and even a little local coffee. I didn't eat at the Bite this time but it is right across the street and has great choices I have enjoyed before. Highly recommend and would stay here again.
Top guest favorite
A popcorn container filled with various snacks, including candy bars and popcorn, is placed on a countertop. Two remote controls are located next to the container, and a light switch is visible on the wall in the background.
Cottage in Prineville
5 out of 5 average rating, 100 reviews

~Quail Run Cottage~

MelissaRating, 5 stars1 week ago
From the moment we drove up, our stay was fantastic! She is the most responsive host and so kind. We had everything we needed and loved being close to it all, yet just out of town. And the bed…. Yep, most comfortable bed we’ve ever slept in away from home, which was needed after a long day of adventure in the Ochocos! Thank you for everything Tera! We will be back!

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