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

Find and book unique ski-in/ski-out homes on Airbnb

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Popular amenities for Southern Oregon ski-in/ski-out rentals

Family-friendly, ski-in/ski-out home rentals

Home in Crescent
4.88 out of 5 average rating, 16 reviews

Beautiful Cabin w/in Minutes of Outdoor Recreation

IlseRating, 5 stars19 months ago
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!
Home in Bend
4.71 out of 5 average rating, 141 reviews

Sunriver Private Home, Private Dock , Plus Hotub.

ShelaghRating, 5 stars10 months ago
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.
Guest favourite
Farm stay in Ashland
4.98 out of 5 average rating, 58 reviews

Meadow House at Willow-Witt Ranch (Farm Stay)

MichaelRating, 5 stars10 months ago
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.
Guest favourite
Cabin in Lakeview
4.94 out of 5 average rating, 134 reviews

Squirrelville

KathyRating, 5 stars4 days ago
What a lovely, peaceful place.We appreciated rustic, historic cabin. The decor was spot on and added to its charm. The surround woods and artesain well water made the tranquility complete.
Guest favourite
Cabin in Bend
5 out of 5 average rating, 47 reviews

Blinn's Landing: Riverfront Cabin, Mountain Views

SamRating, 5 stars9 months ago
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!
Superhost
Home in Bend
4.83 out of 5 average rating, 82 reviews

Cozy & Upscale in Beautiful Bend

Martha LuciaRating, 5 stars10 months ago
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.
Guest favourite
Home in Bend
4.91 out of 5 average rating, 200 reviews

Cinder Butte House

BrookeRating, 5 stars1 week ago
My family of 14 (extended) were in town for my niece's wedding and this house was perfect for our 3 night stay! David was a responsive and friendly host.
Farm stay in Ashland
4.85 out of 5 average rating, 35 reviews

Farmhouse Studio at Willow-Witt Ranch (Farm Stay)

TriciaRating, 5 stars43 months ago
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!

Ski-in/ski-out cabin rentals

Cabin in Ashland

Cabin #17 at Hyatt Lake Resort

RaeRating, 5 stars8 months ago
The little cabin was perfect in every way! We will be back for sure.
Cabin in Crescent
4.95 out of 5 average rating, 37 reviews

Perfect Crescent Lake Area Cabin Retreat

NeilRating, 5 stars9 months ago
Bob and Carrie were great! They helped us deal with the crazy situation where we may have had to cancel due to the wildfires. Always responsive and more interested in our wellbeing than the fact that we were renting the place, they were willing to refund 100% if we had to back out at the last minute. The house is fantastic, it made our family trip wonderful and intimate. Everything that one would want to see is easily within a hour to halfhour away. We would absolutely rent here again and we cannot recommend them enough.
Cabin in Ashland

Cabin #14 at Hyatt Lake Resort

StacyRating, 5 stars4 months ago
We had a great stay! The on-site restaurant and staff were amazing!
Cabin in Ashland

Cabin #13 at Hyatt Lake Resort

YashasRating, 5 stars9 months ago
very good place to stay in middle of the woods, I highly suggest spending more time in the cottage and experience the nature
Cabin in Ashland

Cabin #11 at Hyatt Lake Resort

BrookeRating, 5 stars2 months ago
The cabin was clean and the area is beautiful and quiet! Very relaxing weekend! Plan to go back soon!
Cabin in Ashland

Cabin #3 at Hyatt Lake Resort

GretchenRating, 5 stars2 months ago
We enjoyed our stay here. A cute little cabin in the woods!
Cabin in Ashland

Cabin #2 at Hyatt Lake Resort

Cabin in Ashland

Cabin #7 at Hyatt Lake Resort

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