Southern Oregon Ski Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Ski vacation packages in Southern Oregon

Price found within the past 48 hours. Click for updated prices.

McCall House Boutique Inn

Historic Downtown District

$846

per person

Dec 19 - Dec 23

found 19 hours ago

Roundtrip non-stop flight included

Boise (BOI) to Medford (MFR)

9.2/10 Wonderful! (616 reviews)

Our favorite hotel In Ashland. It is probably the most beautiful building in Ashland and the rooms and the amenities are first class. We recommend this place to everyone.

Reviewed on Oct 13, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

3 Night Ski vacations in Southern Oregon

Price found within the past 48 hours. Click for updated prices.

McCall House Boutique Inn

Historic Downtown District

$763

per person

Nov 19 - Nov 22

found 3 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Medford (MFR)

9.2/10 Wonderful! (616 reviews)

Our favorite hotel In Ashland. It is probably the most beautiful building in Ashland and the rooms and the amenities are first class. We recommend this place to everyone.

Reviewed on Oct 13, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

4 Night Ski vacations in Southern Oregon

Price found within the past 48 hours. Click for updated prices.

Red Lion Hotel Rogue Regency Medford Airport

$725

per person

Dec 19 - Dec 23

found 19 hours ago

Roundtrip non-stop flight included

Boise (BOI) to Medford (MFR)

8.6/10 Excellent! (3,269 reviews)

The hotel was very quiet. The rooms were large and laid out well (sink in separate room from toilet/shower). The free "continental breakfast" actually had scrambled eggs, bacon, and diced potatoes! The only negatives were skimpy towels, a difficult to operate TV, and blackout blinds were not wide enough to stop all light from coming in.

Reviewed on Oct 18, 2026

Ashland Hills Hotel & Suites

$726

per person

Dec 19 - Dec 23

found 19 hours ago

Roundtrip non-stop flight included

Boise (BOI) to Medford (MFR)

8.8/10 Excellent! (1,541 reviews)

Stratford Inn

Siskiyou-Hargadine Historic District

$753

per person

Dec 19 - Dec 23

found 23 hours ago

Roundtrip non-stop flight included

Boise (BOI) to Medford (MFR)

9.4/10 Exceptional! (1,796 reviews)

Wonderful location and very friendly, helpful staff. However it is the first hotel in 20 years of traveling that didn't have a hair dryer in each room.

Reviewed on Oct 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

What are some things I should consider when booking a Southern Oregon ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Southern Oregon ski packages?

Right now, ski trips start at just $725. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Southern Oregon?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Southern Oregon. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Southern Oregon cost?

Sensational ski trips to Southern Oregon start from $725. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Southern Oregon?

The best time to hit the slopes in Southern Oregon depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Southern Oregon ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Southern Oregon ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Southern Oregon with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Southern Oregon ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

Top Ski Southern Oregon Hotels

Hunters Hot Springs Resort

18088 N. Rt. 395 Lakeview OR

1 hour drive from Crater Lake National Park

Stay at this motel in Lakeview. Enjoy free WiFi, free parking, and hot springs on site. Popular attractions Old Perpetual and Lake County Fairgrounds are located ...

7.2/10 Good! (124 reviews)

A little pride would go a long way!

"Hotel was hard to find, no lights on signage or in lobby building. At checkin the card machine was broken. No explanation of amenities, hot spring pool location (again with no lights) and was not clean. Room had broken lights, FIRM mattress and broken shower towel rack. Mold growing in cracks of ..."

Reviewed on Nov 23, 2017

SureStay by Best Western Lakeview

414 N G Street Lakeview OR

1 hour drive from Crater Lake National Park

Book a stay at this business-friendly hotel in Lakeview. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lake County Museum and Schminck ...

8.2/10 Very Good! (652 reviews)

"a little mix-up with the check in being overcharged but they fixed it by checkout. breakfast was better than average. only issue is the water...which has nothing to do with the hotel...a little murky, and would not recommend for consumption"

Reviewed on Oct 11, 2026

Executive Inn & Suites

411 North F Street Lakeview OR

1 hour drive from Crater Lake National Park

Book a stay at this ski hotel in Lakeview. Enjoy free WiFi, free parking, and downhill skiing on site. Our guests praise the helpful staff in our reviews. Popular ...

See all 1,432 properties in Southern Oregon

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.