Family-friendly vacation rentals in Madras

We loved our stay! This house has the best equipped kitchen of any vacation rental we have ever stayed in. The house was decorated for Christmas, a sweet touch. It was a perfect place to spend the weekend, we will definitely be back! Angela was very kind and a great host!

We had a wonderful stay at Rosemary and Steve's chalet- it even had festive holiday decorations, which added a lot of charm! The kitchen had every implement, dish, pan, utensil we could ever want, even a crock-Pot which we use to make a pot of split pea soup that we enjoyed after our day boarding on the mountain. We didn't make use of any of the resort amenities, so I can't speak to any of them, but we did enjoy the hot tub. And had some nice relaxing dog walks around the peaceful grounds of the resort. But best of all was just hanging out all together, playing board games around the big dining table. All in all a wonderful way to spend Christmas!

The house is so cute and had a good size yard for my dog. The hot tub was nice and private. The house is close to this yummy bagel shop and a little market. Paul was great and so sweet. I will definitely be back to this place.

We had a fantastic stay. House was immaculate, well furnished, very spacious, and very comfortable. Kitchen was incredibly well appointed for a rental. Not only would we stay there again, but we wanted to book for another stay in February but this house was already booked...so we booked another rental nearby managed by the same company.

Wonderful space with everything you need for a nice vacation. The location was excellent and walkable to shops and restaurants.

The house is great with a perfect layout for folks to have their own space along with a big gathering area.

My family and I spent the weekend in Sun River and stayed at this Airbnb. It was great! The hot tub was a nice bonus, and the yard was super cute. The place was really easy to find and close to the village. We had a wonderful time and would definitely stay again!

A fun and funky find near downtown. Communication was clear and response was fast. Would definitely stay again…

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.

Karen and John’s place was perfect for us. We were visiting for a wedding at Aspen hall. We drove to downtown Bend and were close enough to town to enjoy the city and walk around. Close to trails for mountain biking and trail running. The space was clean and had everything we needed. Laundry was great addition to Super nice to have a space that allowed dogs too. Karen and John were very responsive and gave all the necessary information for our stay making it a super convenient and carefree experience. Would love to come back again.

Okay, this is an absolutely great location. Super close to pretty much anything you would want to do in Bend and it includes garage storage for larger gear! I was able to quickly get to the Bend River Trail for runs, walk to restaurants in Old Bend, and just generally enjoy the area without my car. Driving from this location was super easy if you need to go a longer distance. The place is really well done and they are pet friendly! Thank you for hosting my cat, Aesop, he enjoyed traveling with me greatly. The only thing I really want to point out is that the hosts call out the stairs up to place as a hazard for older pets and I want to point out that the ladder to the loft (main bed) is really steep. I thought it would be less so and, unfortunately, Aesop had trouble navigating it. If you intend to be highly intoxicated or take really strong sleeping meds, I would suggest not booking this place, as the ladder is a bit treacherous. Otherwise, this place is amazing!

Everything was wonderful! Hope to stay again in the future!

Susan’s place was so clean and comfortable! It was beautiful with lots of thoughtful touches throughout. The plush carpet was excellent and the heated toilet seat, towel rack, and floor were an awesome bonus! The kitchen was well stocked and had everything we needed. The bunk room was perfect for our kids and was such a fun theme! The pack n play was even set up for our littlest one already when we arrived. Little things like that just made it stand out. There was even extra toothbrushes, toothpaste ect that came in handy as one of our kids always seems to forget one. The bonus room above the garage was the perfect addition. I would say besides the bunk room it was the kids favorite spot. We enjoyed movie nights over there with the cozy couch and bean bags! There wasn’t one negative thing about the house or our experience. We want to book it again already for next year!!! We will definitely return!!!

I had an absolutely wonderful stay at Carlie's guesthouse. The location is stunning- peaceful, beautiful and perfect for a relaxing getaway while still being easy and quick to get to Bend. The space itself was incredibly clean, private and well-maintained. The bed stood out as being very comfortable with high quality bedding and pillows, much appreciated. Overall, this has been one of my best Airbnb experiences to date.

Exactly what we were looking for. A cute and cozy spot for a quiet weekend vacation.

The sharpest kitchen knives Ive ever experienced in a rental. Super easy, as advertised. Low stress

Another wonderful stay at Tracy’s lovely, well-stocked and spotless guesthouse! Loved the hot tub, wood stove, fresh eggs and scones, and the gorgeous setting. Perfect location for skiing at mt bachelor and hiking at smith rock. Tracy is always super responsive. We hope to return again soon!

This was a great place to stay, very convenient to Mt Bachelor ski slopes while still in Bend, close to a lot of fun places to eat. I thought this place lived up to the "Ski House" name of the complex. It had everything needed and was comfortable and quiet. The host gave excellent instructions and stayed in contact to insure all went well, which it did! I definitely plan to return.

We had a lovely time at this house. The place was very clean and provided everything we needed. We loved the DVDs and board games. Heating worked well. Everything was as described. The hosts were very communicative. Our kids had fun. We can see ourselves returning there.

Our third visit. Beautiful, but cold wintry weekend to reset and relax. Tollgate is a peaceful community with easy access to Sisters restaurants and to the wonderful surrounding mountains and wilderness areas. We'll be back!

We had a wonderful stay at Emily and Will’s house! The location is at a perfect spot on the ranch. We loved going on walks to the babbling brook and boardwalk to the meadow. We made an early Thanksgiving dinner at the house and their kitchen was fully stocked with everything imaginable. The house itself is decorated beautifully with attention to detail. On top of that, Emily and Will were accommodating to some special requests and were quick communicators. Would definitely stay here again!!

Great spot to stay for a few days of skiing and sun in Bend. Thank you!

The house was comfortable with great spaces for eating indoors and out. We baked and made several meals in the well-stocked kitchen. We enjoyed both decks and the hot tub and saw deer, squirrels and lots of birds from the house. The location is quiet and an easy bike ride to the Cardinal Landing bridge, SHARC, and the village. Would definitely stay here again!

We had a great New Year’s vacation here. Quiet location that is super close to everything you could want to do in Bend. Jill was so friendly, responsive and overall a wonderful host!