Ski-in/Ski-out holiday rentals in Southern Oregon

Our group of 6 really enjoyed staying at Carrie and Bob's for a long weekend. The kitchen was very well stocked with anything you could dream of. The house had so many things from books to games to a good fridge, new washer and dryer, in a beautiful setting. Carrie was great to work with and she always communicated immediately very nicely and well. A great place to vacation in!

Oleksandr was great. The house was clean and comfortable. The host was great at responding and was incredibly helpful.

We had a wonderful weekend at Diane’s place. Hopped into our inner tubes off the dock and floated to harpers bridge. So relaxing! Spent lots of time on the deck looking at the river. Bring your mosquito repellant for the evenings. The kitchen and main living areas are very spacious and all furniture was comfortable. Cozy home.

We needed a place to have down time from my Son’s lacrosse tournament. This place had all space we needed, in great conditions. It was 10 min drive to downtown a most places we needed to go. Very peaceful home away from home. Dorota was proactive contacting us before check in, giving us the flexibility to arrive a bit early.

Great stay in Southwest Bend! Plenty of space for friends and family. Enjoyed the house and outdoor patio!

Great weekend away at an awesome house! Would absolutely book a stay again!

Great location, perfect house and amazing host. Very responsive and always here to help. I would really recommend it to everyone. Very quiet location, with lot of wildlife, even small rabbits greeting you in the morning. Very convenient house and warm. Will come back !

Our group of 6 really enjoyed staying at Carrie and Bob's for a long weekend. The kitchen was very well stocked with anything you could dream of. The house had so many things from books to games to a good fridge, new washer and dryer, in a beautiful setting. Carrie was great to work with and she always communicated immediately very nicely and well. A great place to vacation in!

We had a wonderful weekend at Diane’s place. Hopped into our inner tubes off the dock and floated to harpers bridge. So relaxing! Spent lots of time on the deck looking at the river. Bring your mosquito repellant for the evenings. The kitchen and main living areas are very spacious and all furniture was comfortable. Cozy home.

The owner and staff were fantastic. The Meadow house was peaceful with a great view of the meadow with wetlands. Our family enjoyed the Sandhill Cranes and deer. The Ranch does a great job offering to involve the guests in the daily farm chores and has a lot of great information about the Ranch and surrounding natural features.

My partner and I can’t get enough of Squirreville—it’s our go-to escape from the “real world.” The moment we step into the cabin, we’re wrapped in this incredible sense of warmth and ease. The property itself is stunning, and the landscapes beyond are breathtaking. Cam and Christine are the kindest hosts—always so thoughtful, responsive, and genuinely dedicated to making sure every guest feels right at home. It’s pure magic every time we visit- I cannot recommend this place enough!

Carla’s cabin was incredible. It’s a real genuine log cabin and felt like staying in a bit of history. It was more like staying at your grandparents cabin than an airbnb. She really thought of everything to keep the kids and adults entertained. The cast iron collection is legendary and the rustic touches around the place were perfect. We will be back as often as we can!

We needed a place to have down time from my Son’s lacrosse tournament. This place had all space we needed, in great conditions. It was 10 min drive to downtown a most places we needed to go. Very peaceful home away from home. Dorota was proactive contacting us before check in, giving us the flexibility to arrive a bit early.

Great stay in Southwest Bend! Plenty of space for friends and family. Enjoyed the house and outdoor patio!

This place is an experience! Coyotes howling at night, farm animals out the window, beautiful fog and wonderful hosts. The drive is a little hairy and far out, but totally worth it. If you’re a light sleeper, be wary of farm dogs that bark all night. Didn’t bother us, but we woke up a few times. We will absolutely book again when coming to Ashland!