Cottage holiday rentals in Painted Hills

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.

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.

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.

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.

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.

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.

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!

Tera's property was very conveniently located to everything we wanted but was also in a very country and peaceful location. The cottage was spotless! She is very responsive and helpful and we had no issues at all. Would definitely recommend staying here! Also not too long of a drive to all the things you'd want to do in Bend (:

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!

Such a cute little cottage. A breath of fresh air being inside 🩵 Would definitely recommend and keep in mind for next trip!

While I really enjoyed the artistic flair to this spot, I was really impressed with the infrastructure that was added to make it truly functional. Anyone can add a bunch of bunk-beds to a basement and call it a guesthouse, but a strong level of functionality has been strived for - and achieved. The extra showers had high-powered fans, each bunk had a hook to hang things and a light to read by. There were ample outlets and sinks. So aesthetics AND functionality! Awesome. Got to meet the legend Barbara. She's an empowered soul who is lifting up a town.

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!

Dayville, Oregon is almost the back of beyond given its remoteness, but we could not have had a nicer place to stay for the one night we were there. David, a very pleasant, likable host, greeted us upon arriving. The Fish House is on a beautiful and quiet property with green lawns and trees and wide-open views of the night sky. The Blue Lagoon is rustic on the outside but very comfortable, clean and well accommodated on the inside Including an air-filter which given that it is fire season in this dry wild corner of Oregon was unexpected and very thoughtful. Bed was really comfy. Everything in Dayville is walkable so we headed down to the Dayville Cafe and had a nice dinner. We recommend the pie which we had for breakfast. Should we find ourselves in Dayville again we will definitely return. Do not hesitate to stay at the Fish House. Thank you David and family.

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!

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.

It was a wonderful stay we hope to return soon!

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!

Tennise was wonderful. She let us know her home was ready early and we could check in if that’s what we wanted to do. Location was perfect. Five blocks from the quilt show shops and restaurants. It was too hot for us to be able to enjoy the backyard but it’s beautiful full of flowers. Tennise gave us a tip about where we could see the three sisters and a place for fishing. Great host.

We loved staying here! Clean, comfortable and cozy. Great aesthetic! Perfect for our ski week. Walkable yet calm. We hope to return!

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! :-)

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.

This is the perfect place to stay if you climb at Smith Rock and want to be close to restaurants and breweries afterward.

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.

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.