Cottage vacation rentals in Sisters

Find and book unique cottages on Airbnb

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Popular amenities for Sisters cottage rentals

Cottage rentals with a hot tub

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.
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.
Guest favorite
Cottage in Bend
4.9 out of 5 average rating, 134 reviews

Quaint Cottage Meets Modern Charm, 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!
Superhost
A welcoming outdoor space features a fire pit surrounded by white adirondack chairs, offering options for relaxation. A vintage bicycle is placed nearby, adding charm. A small guest house is visible in the background, with greenery and trees enhancing the serene environment.
Cottage in Old Bend
5 out of 5 average rating, 6 reviews

Perfect spot for groups & families

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

Top guest favorite
Cottage in Bend
5 out of 5 average rating, 38 reviews

Cloudchaser Cottage: Cozy Get-Away

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, 91 reviews

~Quail Run Cottage~

Guest favorite
Cottage in Bend
4.94 out of 5 average rating, 157 reviews

One Block to Downtown, Hot Tub, Private Home, Yard

Private cottage rentals

Top guest favorite
Cottage in Bend
4.95 out of 5 average rating, 418 reviews

Vintage Pink Hot Tub✓ Walkable✓

MarinaRating, 5 stars5 days ago
We had the great stay and instantly fell in love with this charming pink vintage getaway. Every detail felt so thoughtful — from the cozy decor to the super comfy bed. The place was sparkling clean, perfectly central, and had everything we needed, and the hot tub? Our dog felt right at home too. We’re already talking about our next visit — we’ll definitely be back! Thank you!
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 stars1 week 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, 282 reviews

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

ColleenRating, 5 stars3 weeks ago
This place was perfect for a quick business trip! The hot tub and view of the stars was wonderful in the evening. The fenced yard was perfect for our dogs tagging along. We so appreciated the extras such as the provided dog bed and towel. We also loved that the cleaning list was short and that the owners don’t let food go to waste. Overall, the home was quirky in a good way and worked great for our needs!
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

Quaint Cottage Meets Modern Charm, 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

  1. Airbnb
  2. United States
  3. Oregon
  4. Deschutes County
  5. Sisters
  6. Cottage rentals