Cottage holiday rentals in Painted Hills

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!

Great location and space in sisters! As described!

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!

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.

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!

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!

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.

We had a great stay! House was very clean and Kenny was a great host

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!

Great place to stay for a quick overnight 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.

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.

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 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.

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.

It was a wonderful stay we hope to return soon!

Loved this lil house! Close to everything! The hooks in the rooms are perfect! It is a very well thought out living space. They have everything you need and it’s adorable!

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!!! ⭐️⭐️⭐️⭐️⭐️

Quaint and quiet. Clean and great location. Met our expectations. Super friendly hosts and very responsive. Have already recommended to friends.

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!

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.

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.

West Minister Square cottage was a fantastic stay! The cottage was extremely clean, the photos on the listing match reality. The cottage decor and little touches made it a comfortable and desirable stay. All needed amenities were available. Hosts were responsive, instructions were clear. The area around the cottage was very walkable and convenient distance from many attractions. There was room for 2 cars at the property, hosts provided helpful info on how to access property/parking, it was slightly tight to get into. Both entrances to the property were gated and felt very safe. I would definitely stay at West Minister Square cottage again!

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!