Cottage vacation rentals in Sisters

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Popular amenities for Sisters cottage rentals

Cottage rentals with a hot tub

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, 38 reviews

TruNorthwest Retreat | Walk to Town • Pool • Dogs

GailRating, 5 stars3 weeks ago
If you’re seeking a place close to downtown Sisters this is the perfect place to stay. While it might not have the wooded charm of Black Butte, we loved the setting for its walking distance to Sisters Coffee Co. and other shops. The house is so thoughtfully supplied with everything you might want for cooking in the kitchen or relaxing on the comfortable furniture. We really appreciated the fluffy towels and bedding.
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 Bend
4.89 out of 5 average rating, 307 reviews

The Blackberry Cottage

TylerRating, 5 stars7 months ago
We really enjoyed staying at Tomi’s place. Our dog loved the fully fenced in backyard! The home was very clean and the neighborhood was quiet.
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, 25 reviews

Cottage Live/Play in the Heart of Downtown Sisters

CarolineRating, 5 stars5 months ago
Fantastic cottage and location. We added nights onto our stay and did not want to leave. Highly recommend. David and Victoria gracious hosts and Jill the manager added the finishing touches to exceptional customer service.
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, 137 reviews

Guest Favorite! Prime West Side Location, Hot Tub

KatieRating, 5 stars1 month ago
This was one of the most convenient places I’ve stayed in Bend. Super walkable with lots of food options close by. It was also great to walk our daughter to the playground at Harmon park, then to Drake park to enjoy the river. The fenced yard in the back was great for our dogs. There’s also a grassy fenced yard in the front too but one of my dogs could jump over it. The Airbnb had all necessary amenities and we had a wonderful time! Would definitely recommend.
Top guest favorite
Cottage in Bend
5 out of 5 average rating, 38 reviews

Cloudchaser Cottage: Cozy Get-Away

Sarah Rating, 5 stars1 month 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, 11 reviews

Hot Tub, Fire Pit, Dog Friendly by @pinpointstays

VanessaRating, 5 stars2 days ago
Kenny's home and grounds were beautiful. The area was quiet and the backyard was so peaceful. Fun outdoor games, nice hot tub and lots of seating. Plenty of space in the home for everyone in our group. Minutes from downtown Sisters. We would definitely visit again!
Top guest favorite
A hot tub is illuminated by soft string lights against a wooden fence. The water surface shows gentle ripples, indicating bubbling jets, while a relaxing atmosphere is created by the warm glow surrounding the tub.
Cottage in Prineville
5 out of 5 average rating, 93 reviews

~Quail Run Cottage~

RyanRating, 5 stars3 days ago
We had a wonderfully cozy two-night stay. The space is charming and comfortable, thoughtfully stocked with plenty of coffee, snacks, and amenities to make the visit enjoyable. It’s conveniently located near many high desert attractions. The host communicated well throughout. We would absolutely stay here again!
Superhost
A cozy living area is highlighted by large windows allowing ample natural light. A dark sofa adorned with decorative pillows faces a wooden coffee table. A wall-mounted television and art pieces complement the space, while a dining area with chairs is visible in the background.
Cottage in Redmond
4.86 out of 5 average rating, 59 reviews

Come Stay and Play at Little Les Cheneaux Retreat

ChereRating, 5 stars7 months ago
This home is perfect for a family with kids and a pet. Walking distance to the pool, very well equipped with everything you may need including a crock pot! Elizabeth and Daren were extremely fast responding, even with a last minute change request. We will definitely stay again. I recommend this home to anyone looking for a quiet getaway.

Pet-friendly cottage rentals

Guest favorite
A charming cottage is set amidst lush greenery, featuring a light-colored exterior with decorative window accents. A welcoming porch leads to the front door framed by a gabled roof, while a wooden fence encloses the yard, enhancing privacy and inviting a sense of warmth.
Cottage in Old Bend
4.91 out of 5 average rating, 126 reviews

2 Bedroom Delight In The Old Mill

LauraRating, 5 stars1 month ago
We love staying at The Sparrow cottage! This is the second year that my son and I have stayed here and we are already counting the days until we return! We came for Spring Break to visit our friends and get some snow/ski time. (we live in Hawaii :) The cottage is perfect for us! The location is great - you can walk to the Old Mill District, go ice skating at the pavilion, or grab your gear and head up to Mt Bachelor with ease. We love the quiet, peaceful neighborhood and the coziness of the cottage too. After a day of skiing or hiking in the crisp weather, it is nice to come home and snuggle by the fire and watch a movie. Ashley and Mona were amazing hosts - they brought us warm, fresh bread and offered great recommendations for restaurants and local spots. See you next March! Aloha!
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
4.88 out of 5 average rating, 65 reviews

Blossom Cottage Studio

OpalRating, 5 stars1 month ago
Such a cute little cottage. A breath of fresh air being inside 🩵 Would definitely recommend and keep in mind for next trip!
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
4.9 out of 5 average rating, 296 reviews

Quiet central Oregon desert retreat with a view!

LeslieRating, 5 stars2 months ago
Had the best time! Wonderful and peaceful retreat. We enjoyed the amazing views, playing in the yard, and even doing some cross country skiing from the front door in the fresh snow. The house was spotless, beds comfortable, and kitchen fully stocked for us to cook all our meals and feel right at home while being away from home. Wonderful experience!
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 Old Bend
5 out of 5 average rating, 9 reviews

Greeley Cottage: Steps to downtown Bend

TaegannRating, 5 stars1 week ago
We absolutely loved our stay at the Greeley Cottage! The space was perfect for my partner, myself and our dog! It was a very short walk to a lot of great local restaurants, bars and shopping. And a short drive to a lot of other great spots within town. When we checked in, there were some issues with the batteries in the keypad lock, but the host was very quick to respond and assist with getting us checked in! Everything we needed for our short stay was in the unit, which made for a very comfortable getaway. We would definitely love to come back sometime soon!
Guest favorite
Cottage in Old Bend
4.96 out of 5 average rating, 255 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

SarahRating, 5 stars2 weeks ago
The house is so comfortable and conveniently located in Old Bend. You can walk 7-15 minutes in any direction of the house and get to a variety of shops, restaurants, bars, coffee shops and river trails. We didn't drive our car for 3 days and were able to walk to lots of fun stuff. The house is quiet, immaculate and well cared for. The clean hot tub is in the privately-fenced side yard. We would definitely stay here again.
Top guest favorite
The living area displays a light and airy design with two gray sofas and a round table set with four chairs. A neutral area rug covers the floor, while a wooden coffee table is positioned centrally. Soft lighting complements the relaxed atmosphere.
Cottage in Bend
4.98 out of 5 average rating, 107 reviews

The Tumalo House

JayRating, 5 stars1 week ago
Great place to stay! Location was key and this place was perfect. Easy to walk to the Bite also! Would recommend others to stay here.
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 stars2 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, 57 reviews

Court St. Cottage | Downtown Prineville Getaway

JocelynRating, 5 stars1 month ago
I've gotten used to being disappointed by AirBnBs, but Christian's place was an exception. The house was super clean and very functional, but also comfortable. The kitchen is stocked with all the basics, making cooking easy. The bathrooms also had ample supplies. The location is great- very quiet neighborhood but walkable to main strip. We would definitely stay here again.

Private cottage rentals

Top guest favorite
Cottage in Bend
4.95 out of 5 average rating, 419 reviews

Vintage Pink Hot Tub✓ Walkable✓

MatthewRating, 5 stars1 week ago
We loved our stay here! It was our first time staying in Bend. Jay and Dina were communicative and the cottage was on point. The amenities and hot tub were very nice. It’s a great short walk to town or the river trail. Thanks for having us!
Top guest favorite
A wooden sauna, designed in an oval shape, is positioned in a private outdoor area. Two slatted lounge chairs with blue and white striped cushions are placed nearby, set against a backdrop of green grass and trees, creating a peaceful retreat.
Cottage in Sisters
4.98 out of 5 average rating, 158 reviews

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

KatieRating, 5 stars2 weeks ago
Absolutely recommend staying at Debbie's place! The house was even better in person than in the pictures/description! Debbie's home was inviting and everything we needed for our girls weekend! Debbie was an excellent host and very responsive! It was super walkable to downtown and just what our group needed!
Guest favorite
The living area features a cozy sofa and a wooden coffee table atop a woven rug. Large windows invite natural light, while a television is positioned on a wooden stand. A dining area can be seen in the background, enhancing the open layout.
Cottage in Old Bend
4.94 out of 5 average rating, 117 reviews

Two Bedroom Charmer with Hot Tub

TorkelRating, 5 stars2 months ago
We loved staying here! Clean, comfortable and cozy. Great aesthetic! Perfect for our ski week. Walkable yet calm. We hope to return!
Guest favorite
A wooden deck is surrounded by lush greenery and tall trees, featuring a patio set with a large umbrella. A cozy seating area is arranged with striped chairs and a table, creating an inviting outdoor space for relaxation.
Cottage in Bend
4.93 out of 5 average rating, 283 reviews

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

LaurenRating, 5 stars2 weeks ago
We loved this place so much!! The sweet vintage kitchen as the center piece to the home really felt cozy and worked great for our family. All the rooms and bedding was decorated beautifully. My daughter loved the bunk beds in her room and our bedroom was so serene and comfortable. The hot tub on the back porch was amazing! We started almost every day off with a soak. Our doggies loved the fenced in yard and deck for taking naps. The neighborhood is so killer! Walkable to so many cool places in Bend! This is definitely gonna be our go to Airbnb when we visit! Thanks for everything! :-)
Top guest favorite
Cottage in Bend
4.97 out of 5 average rating, 119 reviews

Exceptional Downtown Cottage-Level II EV charger

ParkerRating, 5 stars3 weeks ago
Don’s cottage in Bend had it all. The location was perfect—just a short distance from downtown, but it felt like a peaceful retreat. The location is private and serene with a fair amount of wildlife — squirrels digging for nuts, birds chirping and even white-tailed deer munching on the lawn right in the backyard. The trail behind the cottage that winds along the Deschutes River was a gorgeous bonus. The cottage itself felt like home—cozy, welcoming, and stocked with everything one could possibly need. Don was a fantastic host, and would happily stay here again.
Guest favorite
The front yard features a well-maintained grassy lawn surrounded by a low wooden fence. A clear pathway of brick pavers leads to a covered porch, framed by lush greenery, providing a serene entryway to the cottage.
Cottage in Old Bend
4.96 out of 5 average rating, 255 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

SarahRating, 5 stars2 weeks ago
The house is so comfortable and conveniently located in Old Bend. You can walk 7-15 minutes in any direction of the house and get to a variety of shops, restaurants, bars, coffee shops and river trails. We didn't drive our car for 3 days and were able to walk to lots of fun stuff. The house is quiet, immaculate and well cared for. The clean hot tub is in the privately-fenced side yard. We would definitely stay here again.
Guest favorite
The image captures a scenic view of the Deschutes River, featuring calm blue waters with gentle ripples. Green grassy banks line the river, while a few kayakers enjoy the water. The background includes trees and a glimpse of nearby buildings, offering a sense of tranquility.
Cottage in Bend
4.87 out of 5 average rating, 137 reviews

Guest Favorite! Prime West Side Location, Hot Tub

KatieRating, 5 stars1 month ago
This was one of the most convenient places I’ve stayed in Bend. Super walkable with lots of food options close by. It was also great to walk our daughter to the playground at Harmon park, then to Drake park to enjoy the river. The fenced yard in the back was great for our dogs. There’s also a grassy fenced yard in the front too but one of my dogs could jump over it. The Airbnb had all necessary amenities and we had a wonderful time! Would definitely recommend.
Guest favorite
The exterior of the cottage is highlighted, showcasing a welcoming front door painted in a vibrant coral hue. Two bright pink chairs are positioned on the porch, with a landscaped pathway leading through a manicured yard bordered by wooden fencing and tall pine trees.
Cottage in Bend
4.9 out of 5 average rating, 134 reviews

Modern Charm in Historic Area, Hot Tub, Fenced

CarlieRating, 5 stars2 weeks ago
Absolutely loved staying here. It is on a main road that’s fairly busy, but it’s extremely quiet which was surprising to me. The beds are probably the most comfortable ones I’ve ever experienced with an Airbnb. The host was very accommodating with early check in and we will definitely be back!

Destinations to explore

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  3. Oregon
  4. Deschutes County
  5. Sisters
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