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 wonderful and centrally located. We enjoyed our stay and everything was as described in the posting. We would stay again!

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 wonderful time! The home was comfy and had everything we needed while also clean and welcoming. We were in the area for our son’s baseball tournament, and this was a perfect home base for games in Sisters and Redmond. We enjoyed the hot tub and grill on the back patio, rec center, and walking our dog on the trails. We’ll definitely consider staying here again next time we’re in the area. Thank you!

Really enjoyed Dan's place. We have two dogs and they loved the large backyard, especially sniffing for the mule deer that liked to visit the apple tree in the front yard. The outdoor patio with hot tub and pergola was wonderful, inspiring some ideas for our own home when we return. Dan was very accessible and responsive, helping in any way and communicating when he was in the area. The location is great as well - very close to Tumalo and right near the Tumalo Creek Park, and a short drive from everything else in Bend. We'll be keeping this place mind and may have to visit again in the future!

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

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!

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.

The cottage is wonderful, right on the river, incredibly clean and well stocked. There’s a great assortment of water toys too, paddle boards, kayaks, and inflatables. Even better is that Jackie is an amazing host, so welcoming, friendly, and helpful. Fantastic location too!

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

Beautiful furnishings. Well stocked. Clean and uncluttered. Minimal check out responsibilities. Daniel was quick to respond to a question. We will stay here again next year.

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.

We stayed at West Minister square for a long weekend to visit the Painted Hills, and we can't wait to come back. The cottage is adorable and cozy. The interior decoration is a wonderful mix of modern and rustic with every amenity you could want. The host(s) stocked the kitchen with coffee, left a bottle of sparkling water in the fridge, and the wifi was great (hey, that can be rare at a bnb). Every aspect of the interior was thoughtfully laid out and prepared beautifully. The location is in downtown Redmond and you can walk to a variety of restaurants, coffee shops, and parks. It was easy to get to off of the highway. The host(s) were incredibly responsive and communicative. It was an overall wonderful stay. I can't recommend the place enough.

We’ve stayed in Bend before and chose this unit due to the location and the proximity to downtown and The Old Mill district. We were able to walk to many locations in both areas including breweries, restaurants, parks, shops and trails. The unit itself was very clean and nicely decorated. The neighbors were quiet and the beds were comfortable. There was pretty much everything you would need. We’ll definitely stay here again.

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.