The 10 best winter getaways in Oregon

Your ultimate guide to snow, coastlines, and cozy escapes
Cross country skiers in a field with a mountain in the background.
Mt Bachelor

Winter is coming, transforming Oregon into a wonderland of snow-dusted mountains, misty coastlines, and charming small towns. Whether you're craving an adrenaline-filled ski trip, a peaceful retreat by a roaring fireplace, or a cozy coastal escape, Oregon delivers experiences that'll make you forget about your Netflix queue.

In this guide, we'll explore the top places to visit in Oregon this winter—the kind of destinations that remind you why living here beats just about anywhere else.

Mount Hood in winter

1. Mount Hood

Oregon's most famous peak for good reason

  • Why go: No list of Oregon winter escapes is complete without Mount Hood. Just over 90 minutes from Portland, this iconic peak serves up everything from epic snowfall to mid-slope hot springs—yes, really.
  • Must-dos:
    • Skiing & snowboarding: Timberline Lodge—that National Historic Landmark from The Shining—offers year-round skiing and architectural eye candy. Mt. Hood Meadows offers a diverse range of terrain for everyone, from nervous first-timers to aspiring Olympians.
    • Snowshoeing & winter hikes: Trillium Lake and Mirror Lake transform into frozen postcards where your only company is Douglas firs and your own breath clouds.
    • Cozy lodge stays: Hole up in a chalet-style rental with a fireplace, hot tub, and views that'll ruin every other mountain range for you.
    • Unique winter experience: Soak tired muscles at Bagby Hot Springs—a rustic, clothing-optional gem requiring a 1.5-mile snowshoe trek that filters out the uncommitted.
  • Local insider tip: Skip the predictable hot chocolate and grab a seat at Cascade Dining Room for mountain views with your après-ski cocktail. Or keep it real at Charlie’s Mountain View for pub grub that actually tastes good.
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Bend OR

2. Bend

Where powder meets pints in perfect harmony

  • Why go: Bend is where outdoor obsessives meet beer nerds, and somehow it works perfectly. Surrounded by the Cascades and packed with microbreweries, art galleries, and year-round sunshine (relatively speaking), it's the most livable winter destination in Oregon.
  • Must-dos:
    • Ski at Mount Bachelor: 4,300 acres of terrain where the snow stays drier and the lift lines stay shorter than Hood.
    • Dog sledding tours: Mush through snowy forests at Mount Bachelor and channel your inner Iditarod racer.
    • Snowmobiling & tubing: Hit the snow parks for family-friendly chaos that doesn't require a season pass.
    • Hot springs relaxation: Drive to Umpqua, McCredie Hot Springs, or these other nearby hot springs for a soak that'll make you feel like you've discovered Oregon's best-kept secret.
    • Unique winter experience: Take a fat bike tour through snow-covered trails—because regular mountain biking is apparently too easy.
  • Vacation rental tip: Book a modern riverfront home with a private hot tub. You've earned it.
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Coos Bay, OR

3. Coos Bay

Storm watching and coastal grit with character

  • Why go: Coos Bay is Oregon's working waterfront—no curated boutiques or overpriced tide pool tours here. What you get instead: dramatic winter storms, authentic seafood, and a coastline that hasn't been Instagrammed to death.
  • Must-dos:
    • Storm watching: Shore Acres State Park delivers crashing waves against rugged cliffs that make you feel appropriately small and alive.
    • Tide pooling: Winter low tides reveal marine life without the summer tourist stampede.
    • Fresh seafood: Hit local spots for Dungeness crab that was literally caught this morning.
    • Sand dunes exploration: Oregon Dunes National Recreation Area offers 40 miles of windswept beauty for hiking and photography.
    • Unique winter experience: Watch gray whales migrate past the coast from December through January—bring binoculars and patience.
  • Stay tip: Book a waterfront rental where you can watch storms roll in from your living room window.
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Crater Lake National Park in winter

4. Crater Lake National Park

Frozen beauty that makes you believe in magic again

  • Why go: Want nature that’ll make your jaws drop? Crater Lake delivers. Its impossibly blue waters framed by snow-laden cliffs create scenery so dramatic it feels AI-generated.
  • Must-dos:
    • Snowshoeing & cross-country skiing: Glide through pristine snowfields on trails where silence isn't just golden—it's the whole point.
    • Photography & stargazing: Winter skies here are absurdly clear, making it prime territory for astrophotography nerds and casual stargazers alike.
    • Stay nearby in a rustic cabin: Cozy nights by the fire hit different after a day in subzero temps.
    • Unique winter experience: Join a ranger-led snowshoe walk to the rim—it's free, educational, and you'll have the park practically to yourself.
  • Insider tip: Check road conditions obsessively before visiting. Some park entrances close when snow gets serious, but that's exactly when the experience becomes truly magical.
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Wallowa Lake in winter

5. Wallowa Lake

Oregon's alpine secret that actually stays secret

  • Why go: Tucked into the Wallowa Mountains—Oregon's "Little Switzerland"—this spot stays blissfully under-touristed even when it deserves a crowd.
  • Must-dos:
    • Ice activities: When the lake freezes over (and it does), locals break out skates, hockey sticks, and ice fishing gear like it's Minnesota.
    • Snowshoeing and cross-country skiing: The Wallowa-Whitman National Forest offers hundreds of miles for snowmobiling, cross-country skiing, and snowshoeing without the Bachelor lift-line drama.
    • Ride a unique rail bike: Pedal a four-wheeled rail bike through snow-dusted canyons along historic tracks—it's part workout, part scenic tour, entirely unique.
    • Unique winter experience: Ride the Wallowa Lake Tramway in winter for 3,700 vertical feet of views without the crowds—just you, the mountain goats, and the Wallowas stretched out forever.
  • Stay tip: Snag a cozy cabin or A-frame near the lake. You're off-grid enough to feel adventurous but civilized enough to have good coffee in the morning.
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Columbia River Gorge in winter

6. Columbia River Gorge

A winter wonderland of waterfalls and wine

  • Why go: The Gorge transforms in winter from a crowded summer playground into something quieter and more mysterious. Frozen waterfalls, misty trails, and cozy tasting rooms make it the perfect close-to-Portland escape.
  • Must-dos:
    • Frozen waterfall hikes: Multnomah Falls and Horsetail Falls become ice sculptures when temps drop—just watch for ice on trails.
    • Wine tasting: Hood River's tasting rooms offer fireside pours without the summer crowds.
    • Explore Hood River: Visit Hood River at its most quiet—browse shops, galleries, and cafes without summer's chaos.
    • Scenic drives: The Historic Columbia River Highway looks especially moody under gray winter skies.
    • Unique winter experience: Ice climb frozen waterfalls with a guide—it's technical, thrilling, and completely surreal.
  • Stay tip: Choose Hood River for walkable downtown access or find a secluded cabin with Gorge views.
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Sunriver in winter

7. Sunriver

All the mountain perks, none of the rustic sacrifice

  • Why go: Sunriver is where Portland families go when they want all the amenities with none of the roughing it. Think paved bike paths, pools, and enough activities to keep everyone from toddlers to grandparents entertained.
  • Must-dos:
    • Mount Bachelor access: You're 20 minutes from skiing without staying slope-side.
    • Nordic skiing: The Sunriver Resort Nordic Center offers groomed trails through ponderosa forests.
    • Ice skating: The outdoor Village ice rink brings small-town charm with mountain views.
    • Stargazing: Head to the Sunriver Nature Center & Observatory for clear, dark-sky viewing.
    • Unique winter experience: Try snowshoeing at night during full moon tours—eerie, beautiful, and surprisingly popular.
  • Stay tip: Rent a home with SHARC (Sunriver Homeowners Aquatic & Recreation Center) access for indoor pools and hot tubs.
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Depoe Bay in winter

8. Depoe Bay

Intimate coastline for storm chasers and whale watchers

  • Why go: Depoe Bay bills itself as the "Whale Watching Capital of the Oregon Coast," and winter is when it earns that title. Gray whales migrate through, storms batter the shore, and the whole town feels like a secret worth keeping.
  • Must-dos:
    • Whale watching: Gray whales pass through from December to February—spot them from shore or book a charter.
    • Storm watching: The seawall at Depoe Bay creates dramatic wave spray that's equal parts thrilling and soaking.
    • Tide pool exploration: Rocky shores reveal starfish, anemones, and crabs during winter low tides.
    • Cozy cafes: Warm up with chowder and coffee at spots overlooking the harbor.
    • Unique winter experience: Watch the "Spouting Horn" sea cave erupt with incoming waves—nature's own geyser show.
  • Stay tip: Book an oceanfront rental where you can whale-watch from bed with coffee in hand.
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Willamette Valley vineyard in winter

9. Willamette Valley Wine Country

Vineyard views and fireside tastings

  • Why go: Summer brings crowds to the Willamette Valley; winter brings intimacy. Tasting rooms swap picnic tables for fireplaces, and you'll actually get to talk with winemakers instead of jockeying for bar space.
  • Must-dos:
    • Winery tours: Visit acclaimed pinot noir producers like Domaine Serene, Sokol Blosser, or Stoller without reservations booked months out.
    • Farm-to-table dining: McMinnville and Dundee offer restaurants where "seasonal" actually means something in January.
    • Scenic drives: Rolling vineyard hills look particularly moody under winter clouds and occasional snow.
    • Truffle hunting: Join guided truffle foraging tours—Oregon's black truffles peak in winter months.
    • Unique winter experience: Take a winter vineyard hike with a winemaker who'll explain dormant vine pruning while you sip from a thermos.
  • Stay tip: Book a rental in McMinnville or Dundee for walkable wine tasting and small-town charm.
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Brookings coastal view in winter

10. Brookings

Oregon's banana belt, where winter feels optional

  • Why go: Brookings sits so far south that winter often forgets it exists. Mild temps, blooming flowers, and empty beaches make it the anti-winter winter destination—perfect for people who want to escape without the snow.
  • Must-dos:
    • Beachcombing: Hunt for agates, jasper, and driftwood on uncrowded beaches like Myers Creek and Lone Ranch.
    • Azalea blooms: Yes, really—Azalea Park blooms in winter thanks to the temperate microclimate.
    • Hiking: Samuel H. Boardman Scenic Corridor offers dramatic coastal trails without summer's crowds.
    • Crabbing and fishing: Winter is prime Dungeness crab season—catch your own or buy fresh off the dock.
    • Unique winter experience: Explore the natural rock arch at Arch Rock Point during low tide—timing is everything.
  • Stay tip: Find a beachfront cottage where the sound of waves replaces your alarm clock.
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Tips for planning your Oregon winter getaway

  1. Book early: Winter weekends and holidays fill fast—especially at Hood and in Bend. Lock in your rental before Thanksgiving if you want options.
  2. Check road conditions obsessively: TripCheck.com is your best friend. Mountain passes close without warning, and that "light dusting" can mean chains are required.
  3. Invest in proper gear: Traction devices for your boots, waterproof layers that actually work, and a decent ice scraper. You'll use all of it.
  4. Pack for three seasons: Oregon winter means 60°F at the coast, 20°F in the mountains, and rain everywhere in between. Layers aren't optional.
  5. Fill up before you head out: Gas stations get sparse in Eastern Oregon, and you don't want to be that person coasting into Joseph on fumes.
  6. Bring tire chains: Even if you have 4WD. Even if you "probably won't need them." You'll need them.
  7. Choose your rental strategically: Oceanfront homes for storm-watching, mountain cabins with hot tubs for après-ski, lake houses for total disconnect. The right rental isn't just where you sleep—it's half the experience.

Oregon winter hits different—fresh tracks, storm-watching, fireside wine pours, whatever speaks to you. Book your winter escape on Vacasa.com and choose from coastal condos where waves lull you to sleep, mountain cabins with hot tubs and views, or lake houses that make unplugging feel easy.

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