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 place to stay, we loved it! So close to everything in town too

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.

I have been to Bend MANY times over the years, and this was my favorite place to stay. You are just blocks from McMenamins and all of downtown is right at your doorstep. There is also a dog park right before McMenamins that you can take your furry friends to. The hot tub was such a nice touch, and it was really helpful to have a washer and dryer. The internet worked great as well, and the TV had all of our favorite streaming services. 10/10 would recommend booking here.

The house was very centrally located which made walking to downtown or Drake Park very easy. We enjoyed the restaurants that were located within just a few blocks from the house. The bed was extremely comfortable! We have 2 toddlers and it worked out very well for us. We hope to be back soon!

We had a wonderful stay at Williams place. It was everything we needed for the kids and ourselves!! The fun bedroom and play loft in the kids room, to the warm cozy living room , and finally the outside jacuzzi make it the perfect winter getaway for our yearly ski vacation. Thanks for a wonderful stay and we would and can’t to stay there again!!

This house is in such an amazing location. It is perfectly positioned between Hoodoo and Sisters. It only takes a couple minutes to get into Sisters for food and shopping. The neighborhood is very peaceful and is gorgeous as it is nicely nestled in the woods. The house has a very open floor plan which was amazing to visit with everyone. It was easy to play games and make dinner at the same time. Loved this house and will be saving the listing for next time!

Thank you for hosting us! Lovely small cottage with all that you need in a perfect location, plus super nice accommodating hosts :)

Cute and clean little cottage to stay at while in town for a wrestling tournament. Thank you.

we had an issue withe dishwasher and they replaced it right away! Erin was super responsive and available during our entire stay. Would definitely rent here again.

I was impressed with how well the bunkhouse was stocked. Kitchen was stocked with all that we needed along with extra blankets, towels.

Loved our stay. Place was clean and very comfortable. Kitchen had all things we needed and especially enjoyed the freestanding heater in the living room. Great location. Easy walk to downtown Bend and all the shops, breweries and restaurants. Will definitely stay at Mountain Haus again when in Bend again!

We enjoyed our first visit to Bend. The home was adorable and very clean. Location was close to town and very walkable.

Great stay! The location is perfect for walking into downtown Sisters and exploring the many shops. Check in was easy, plenty of space to park. Spacious hangout room and everything you need from the kitchen!

I Should start with we could not have been more pleased with our stay at this adorable place! Ashley’s cottage was just as described! Close to so many wonderful sights and amenities! Warm, cozy and comfortable!! Seriously just adorable! We enjoyed our Thanksgiving dinner there, the cottage had everything we needed to prep a proper meal and then some! We enjoyed playing games in the sun room every morning at the table in the breakfast nook and every evening at dinner time! The bikes were so fun and a big bonus, we loved our ride down by the river, it was so close and easy to get too!! We enjoyed the hot tub every night!! The owners seriously couldn’t have been more communicative with us or accommodating to us! We are just beyond pleased with our stay at this adorable cottage and can’t thank the owners enough for such a wonderful stay! We will most definitely be back!!

This cabin was a wonderful escape for a relaxing getaway! The location was ideal, in a quiet neighborhood, offering both privacy and easy access to nearby attractions and activities. The house itself was cozy and well-appointed, with all the amenities we needed for a comfortable stay. The highlight was definitely the hot tub, which was the perfect way to unwind after a day of exploring. The host Lisa was friendly and responsive, ensuring we had everything we needed. I would recommend this cabin to anyone looking for a peaceful and rejuvenating retreat!

Donald’s downtown cottage is a true gem, and he is the perfect host—warm, considerate, resourceful, and discreet. I almost hesitate to write the review he and the cottage deserve, fearing that it will become so popular I may never get the chance to return, as other lucky travelers discover this special place and keep coming back. Though far from my home in Europe, I felt immediately at ease in this cozy, beautifully equipped cottage nestled within a charming garden.

I have been to Bend MANY times over the years, and this was my favorite place to stay. You are just blocks from McMenamins and all of downtown is right at your doorstep. There is also a dog park right before McMenamins that you can take your furry friends to. The hot tub was such a nice touch, and it was really helpful to have a washer and dryer. The internet worked great as well, and the TV had all of our favorite streaming services. 10/10 would recommend booking here.

The house was very centrally located which made walking to downtown or Drake Park very easy. We enjoyed the restaurants that were located within just a few blocks from the house. The bed was extremely comfortable! We have 2 toddlers and it worked out very well for us. We hope to be back soon!

Loved our stay at Anna’s place! It’s the cutest, homiest little bungalow & is in a fantastic location. We were able to walk into downtown, walk to a grocery store & explore the neighborhood. The house itself is very cute, spacious & very clean. We would 100% stay again!