Cottage vacation 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

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!

This home is perfect for a family with kids and a pet. Walking distance to the pool, very well equipped with everything you may need including a crock pot! Elizabeth and Daren were extremely fast responding, even with a last minute change request. We will definitely stay again. I recommend this home to anyone looking for a quiet getaway.

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!

It was perfect for our family. Cozy and supplied with everything we needed for our trip.

What an amazing place!!! Seriously one of the best Airbnbs I’ve stayed at. Jackie decorated the house for Christmas. So right away felt cozy. The location is awesome. Close to Mt Bachelor for the slopes. Walkable to restaurants, stores and bars. Nice walking along the greenway for the dogs. The kitchen was well stocked. Even had a crock pot which we didn’t use but a detail that I think goes with the house. The interior design def makes the house cozy and not the other lack luster money grab airbnbs. Already thinking of coming back in spring for MTBing.

Great lil home base for our NYE trip! House was cozy and comfy, doggos enjoyed having the yard space. Easy walk to restaurants and downtown. Aaron was also quick to answer any questions I had.

Had another great stay here and will be back!

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.

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.

Really nice place for a larger group and excellent host. Also very close to the ski shuttle for Mt. Bachelor. Would stay again.

Be prepared to melt into luxury & comfort, with the most thoughtful amenities…I’m still dreaming of the water pressure & endless hot water & magnetic shower head…you’ll melt into The Ritz-Carlton-esque bedding and the top of the line mattress. This spot screams warmth, simplicity & taste. The host is genuinely lovely and gracious. Private parking spot, in a safe & security camera monitored alley…safer than most driveway or street parking. The location is the heartbeat of downtown but free standing space is sooo private, with no neighbors lurking over you!