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

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

Top-rated ski-in/out rentals in Southern Oregon

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Grants Pass

4.95 out of 5 average rating, 217 reviews

1940s Vintage apartment steps from the Rogue River

Welcome one and all to DunMovin'. At Riverside on the Rogue you will go to sleep with views of the stars through the skylights and wake up to the Wild and Scenic Rogue just outside your French Doors. Throw a line in and fish from the yard if you like. Lounge by the heated saline pool, feed the geese, go shopping, or head to any of our amazing local restaurants. I'm in the city limits. It's my slice of heaven and I'm sharing it with you. My other unit can be found at: 'The Cottage at DunMovin'

Superhost

Apartment in Bend

4.64 out of 5 average rating, 45 reviews

Rustic Cottage with views of the Deschutes River!

Your private riverside cottage awaits! This condo can sleep up to two people in a full size bed, includes a kitchenette and a large bathroom. With the Deschutes directly out the window, you can't get any closer without getting wet! This condo is owned and designed by Bendistillery and Crater Lake Spirits founder, showcasing that local juniper does not only make great gin, it also makes great furniture! Maximum of 2 pets allowed for an additional pet fee of $55.95/pet, requested after booking.

Guest favourite

Home in Bend

4.91 out of 5 average rating, 193 reviews

Cinder Butte House

This beautiful house is 5 to 7 minutes to the Old Mill District, the city centre, parks, art, cultural attractions, and dining; 20 to 25 minutes to Mt. Bachelor and Cascade Lakes. Guests love the comfortable beds, well-equipped kitchen, the set up, spacious rooms, and the huge back patio with a fire pit, hot tub, numerous tables and chairs, and more. Ideal for families with kids and large groups, the house offers all necessary amenities and plenty of games and toys for both kids and adults.

Guest favourite

Cabin in Bend

5 out of 5 average rating, 47 reviews

Blinn's Landing: Riverfront Cabin, Mountain Views

Book early for Summer 2025! Historic log cabin, located at the confluence of the Spring and Deschutes Rivers, adjacent to Sunriver Resort, offers a relaxing getaway with sparkling natural springs and picturesque mountain & river views. Enjoy an idyllic retreat at this coveted six acre homestead surrounded by the Deschutes National Forest and boasting 780 feet of private pristine riverfront perfect for fishing, river floating, hiking & stargazing. Wonderful work/play escape. Dogs welcome.

Guest favourite

Cabin in Crescent

4.85 out of 5 average rating, 13 reviews

NEW Cozy Mountain Retreat Perfect for Big Groups!

Discover this unique newly built custom home in the highly desirable Diamond Peaks neighborhood. The expansive open concept home has stunning mountain views, two full living rooms and three relaxing large indoor fireplaces. Decompress in the sauna after a full day of exploring the nearby lakes or hitting the slopes at Willamette Pass. In the summer, go fishing or sailing at Crescent Lake or Odell. The ideal place to gather with extended family or friends for a memorable reunion!

Top guest favourite

Home in Sunriver

5 out of 5 average rating, 10 reviews

Chic Sunriver Getaway: Sauna, Spa, & SHARC | River

New to AirBnB! Stylish yet private Sunriver home, perfect for outdoor enthusiasts and relaxation seekers! Access nearby river and mountain bike trails, unwind in the private sauna or hot tub, & relax in front of the fireplace. With an open-concept living area, vaulted wood ceilings, and large windows w/ scenic views, this cozy retreat is a perfect blend of comfort and nature. Enjoy all that Sunriver offers, from hiking and biking in summer to skiing in winter. SHARC passes incl.

Cabin in Crescent

4.81 out of 5 average rating, 111 reviews

Bigham Cabin Crescent Creek

Welcome! Come enjoy the best setting on Crescent Creek. Our Cabin has TWO bedrooms in the Main home with the third and fourth bedrooms in our detached garage. Lots of living space with large sitting areas outside with a view of the creek. The home is located with in 10 miles of Willamette Ski area. We are located close to Crescent Lake. The creek provide a beautiful view and entertainment in the summer. Winter has the best view of creek from the hot tub. There is No Internet.

Guest favourite

Cabin in Lakeview

4.94 out of 5 average rating, 131 reviews

Squirrelville

Squirrelville is furnished, built in the early 1920s and is almost 100 years old! It has one bedroom, open plan living and kitchen area, and 110 V power. Sleeps 2 adults + one child. Bedroom: Queen size bed/dresser. Free standing closet. Woodstove in living room and electric/oil heater. Kitchen area, sink, appliances, dishes, pans, silverware, water. There is a carpeted outhouse, and an outdoor shower (availability contingent on outdoor temps).!

Cabin in Crescent

4.95 out of 5 average rating, 37 reviews

Perfect Crescent Lake Area Cabin Retreat

Welcome to the perfect place to spend with family and friends or to experience a quiet romantic getaway. Relax in this outdoor-themed cabin with comfy furnishings, air-conditioning, WiFi, and a library of movies, books, and games. A detached "bonus room apartment" with a full bath offers privacy and separation of space. The fully equipped kitchen is well stocked with oils, seasonings, and baking ingredients.

Superhost

Home in Sunriver

4.75 out of 5 average rating, 48 reviews

Cozy Place: 8 SHARC Pas, Hot Tub, AC, EVL2 Charge

The cozy family vacation home is close to Mt Bachelor, Sno-Parks, Cascades Lakes, High Desert Museum, Lava Butte and Lava River Cave, Newberry National Volcanic Monument, Smith Rock State Park, downtown Bend, Sisters, Redmond and MANY other outdoorsy adventures, this home is close to all of the best Central Oregon spots and has 8 Sharc passes. It has everything you need. Book and Stay as long as you want to!

Guest favourite

Farm stay in Ashland

4.98 out of 5 average rating, 58 reviews

Meadow House at Willow-Witt Ranch (Farm Stay)

The Meadow House offers a relaxing, off-grid retreat in the Southern Cascades. Escape to a peaceful, private 3-bedroom, 2-bath house overlooking a 100-acre meadow. At 5,000 feet elevation this off-grid home offers the perfect base for relaxation and outdoor adventure. The house includes a well-stocked kitchen, fresh farm eggs and milk, Wi-Fi, and a washer/dryer—everything you need for a comfortable stay.