Cottage holiday rentals in Bend

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

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.

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

Such a whimsical and unique place, and such a beautiful location nestled up against the Badlands. Had a wonderful long weekend looking at the stars and hiking in the sagebrush and juniper. Clearly this place was a labor of love, so many thoughtful touches from the art to the books to the dog supplies. Close enough to Bend to get out to eat but also remote enough to feel like you are in the outback. Thank you!

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.

This place was amazing. It had everything I needed, was centrally located and incredibly clean

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!

Great location and a very comfortable home, just as described. The back deck and hot tub were a bonus. Since the location is close to downtown, the river, and the old mill district, the bikes came in very handy. We'd stay 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!

Anna’s cottage is lovely! Perfectly appointed for a weekend away, the yard was wonderful for our small dog to run around in. Appreciated how communicative and helpful Anna was. Thanks for a great stay — we’ll be back!

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.