United States
Lesser Known But Loved by Locals

This 13-day Luxury Oregon Winter Vacation showcases the breadth of activities and exclusive activities available in Oregon during the winter months. Lesser-known yet loved by locals, winter in the Pacific Northwest can’t be beat. Migrating whales, crashing surfs, white truffle hunts, back country recreation, and hot spring soaks: all shine during the winter months. Add in private helicopter transfers, snowmobile rides, cozy mountaintop cabins, behind-the-scenes winery tours, and you have the recipe for a truly unforgettable trip. From the Cascade mountains to the rugged coast, get ready to experience the Pacific Northwest at its very best with Ker & Downey.


Your Luxury Oregon Winter Vacation kicks off with a bang. After landing in Portland, you will immediately set off in your private helicopter to Mount Hood. Circle Oregon’s tallest peak from the air before landing at the perfect picnic site in the hills. Your private naturalist guide will then transfer you to Timberline Lodge for a history tour of the area and some fireside cocoa. Finally, take a snowcat to your accommodations at an exclusive lodge hidden high in the mountains, where you will enjoy a special welcome dinner prepared by a private chef. You will enjoy two full days of snow activities while here. Whether you wish to enjoy all-day ski-in / ski-out access to the largest ski area in the Pacific Northwest, set out on a glacier snowshoe tour, go sledding, or simply cozy up by the fire — the choice is yours in this winter wonderland.

The next stop on your Oregon Winter Vacation is Bend in Central Oregon. Marvel at the waterfalls of Smith Rock State Park, known as the “Seven Wonders of Oregon.” You will get to explore the falls by land on foot or horseback, then by air via helicopter. Yet again, your helicopter will transport you over the Cascade Mountain Range to your resort accommodations near Bend. A spacial lava cave dinner will welcome you.

Over three days, partake in an endless menu of winter recreation. Set out on a cross-country ski tour to Tumalo Falls and explore the many breweries in Bend on a tasting tour. Additionally, enjoy a guided sled dog excursion or horse drawn sleigh ride. Or perhaps take a snowmobile to the hot springs and learn about night sky photography. Ker & Downey will gladly cater your Oregon Winter Vacation to your interests.

Next, enjoy an overnight near Crater Lake. Winter is truly special in Crater Lake National Park. This area, which centers around the deepest lake in the United States, will feel like it is all yours during an Oregon Winter Vacation. You will have the chance to snowmobile up to the North Rim of the Crater. Next, choose between a full-day cat skiing experience at Mt Bailey or a waterfall and hot springs hike along the North Umpqua.

Oregon’s gastronomy moves front and center in Willamette Valley. January through March is prime season for white truffle hunting in Oregon. As such, a professional truffle dog and trainer/guide will lead you on a truffle hunting excursion. It all ends with a “truffle-inspired” picnic lunch paired with Willamette Valley wine. Then, visit a local vineyard for a hands-on barrel-to-bottle experience. You will have the chance to create an entire barrel of wine, which can be shipped back to your home for many months of enjoyment!

The cornerstone of your Oregon Winter Vacation lies on the Central Oregon Coast. From the Sahara-like desert dunes to the rocky and rugged coastline, this region boasts an otherworldly landscape. While here, take a thrilling ride on a dune buggy through the sand dunes. Tour the most photographed lighthouse in the Pacific Northwest: Heceta Headlight House. Explore the tidepools of Cape Perpetua and achieve uninterrupted views stretching for miles across the coastline. Indulge in a “Local Makers” seafood dinner prepared by a private chef at your luxury lodge. Try your hand at a winter surfing lesson and beachside sauna session. Go foraging for clams and crabs, which are most abundant in winter. Or partake in a fun fat-biking excursion along the beach to remote areas. The choices are endless over your three full days here.

Finally, your Oregon Winter Vacation concludes just as it began: with a private helicopter transfer. First though, you will have a chance to go whale watching in the “Whale Watching Capital of the Oregon Coast,” Depoe Bay. Indeed, winter proves the best time to view the migrating pods of Gray Whales. Your private helicopter will then whisky you away toward Portland, stopping en route for a few more winery tours and tastings in Willamette Valley. A rooftop landing in downtown Oregon brings you to your contemporary luxury hotel accommodations for your final overnight and farewell.

Book an Oregon Winter Vacation

Contact a Ker & Downey destination specialist to customize your own vacation in Oregon, and read more about the seasonality and pricing in North America. For even more travel inspiration, follow us on Instagram, Facebook, and Twitter.