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Get the beanies and rain gear ready, Portland. Winter is on its way, and—as it does every year—it’s bringing a sharp drop in temps and a plethora of wet weather. But don't let the inevitable (and predictable) seasonal change get you down. Our Winter Escapes roundup features great ideas for getting warm, cozying up, or even embracing the frigidity of winter. Explore the recommendations below for a winter experience, or several, you won’t forget!
Village Properties at Sunriver
Enjoy an Adventurous Yet Relaxing GetawayOpens in new window
Sunriver leaves families and outdoor enthusiasts wanting for nothing! This community lives peacefully with our beautiful natural environment that allows visitors all the comforts of home while getting to experience the great outdoors. With stunning riverside trails, 34-plus miles of paved pathways, and the world-class Mt. Bachelor Ski Resort less than 30 minutes away, Sunriver is the ideal destination to spend all day adventuring and then come back to your cozy vacation rental to relax in your private hot tub and stargaze, or curl up by the fire and watch the snow fall outside your window. Use or mention code: WW15 at checkout for 15% off nightly rent. **Applicable to new, direct bookings only. Restrictions may apply; contact us for details.
Where: Sunriver, OR.
Portland Opera
Immerse Yourself in Part of the City’s Cultural LandscapeOpens in new window
Portland Opera is a mission-driven, visionary opera company founded in 1964 and dedicated to enhancing the cultural landscape of the region. Portland Opera gathers and inspires audiences, artists, and collaborators to create shared opera experiences that enliven and connect us all, enhancing the cultural landscape of the beautiful Pacific Northwest. It is Oregon's largest opera company, offering a diverse selection of programming this winter, including works from the inherited canon and the contemporary roster.
Four Portland store locations | Hours: 10 am–6 pm daily.
Oregon Zoo
Stay Close to Home and Connect With CommunityOpens in new window
Every year, ZooLights dazzles visitors of all ages with wildlife-inspired light displays and a whole lot of seasonal fun. It’s the ideal place to gather friends and family, snap photos and make lasting memories. Looking for the perfect holiday date night? Bring that special person in your life to ZooLights. Check out the magical meadow light show, along with a variety of interactive displays. Hop on the zoo train and see dozens of life-size animal lanterns along the route. Walk through vibrant tunnels of glittering lights and take in the glowing festive atmosphere.
Where: 033 SW Canyon Rd.
Taste Newberg
Get Away to Where Oregon Wine Country BeginsOpens in new window
Just 25 miles from Portland, Newberg is where Oregon wine country begins—and where visitors can slow down and savor the season. Newberg blends small-town hospitality with world-class experiences. It’s home to Oregon’s only Forbes Five-Star resort, The Allison Inn & Spa, and a walkable downtown where tasting rooms, boutiques, and farm-to-table restaurants lie just steps apart. Visitors can explore the Oregon Wine Country’s first official water-trail access point on the Willamette River, discover historic architecture and murals, or take part in seasonal events celebrating local makers and chefs. It’s an authentic, close-to-home getaway that feels worlds away. Winter in Newberg means fewer crowds, cozy fireside tastings, and a welcoming community ready to share the very best of Oregon’s food, wine, and art.
Where: Newberg
Columbia Gorge Getaways
Visit a Glamping Resort Nestled on 400 Acres of Reclaimed TimberlandOpens in new window
The property features an array of exceptional accommodations, including luxury yurts, high-end safari tents, cozy bell tents, and pristine campsites, all designed to immerse guests in nature without sacrificing comfort. Onsite amenities range from heated floors and full kitchens to high-speed Wi-Fi, miles of onsite hiking and biking trails, and even a majestic 450-year-old old-growth tree. Whether you’re seeking solitude, adventure, or a one-of-a-kind celebration, Columbia Gorge Getaways offers a rich blend of authenticity and solitude for every kind of escape.
Where: 1101 Bear Creek Road, Carson, Wash.
Abbey Road Farm
Treat Yourself to a Picturesque Destination in Wine CountryOpens in new window
Abbey Road Farm in Oregon’s Willamette Valley features a winery, vineyard, tasting room, and unique lodging in converted grain silos. Guests can enjoy gourmet farm-to-table breakfasts, explore the working farm with animals and gardens, and experience exceptional hospitality. It’s a place where wine, food, and nature come together for a truly memorable stay.
Where: 10501 NE Abbey Road, Carlton
Florence Area Chamber of Commerce
Head South for a Wonderful Winter at Oregon's Coastal PlaygroundOpens in new window
No other destination offers such a diversity of unforgettable fun for friends and family, and all within minutes of enchanting Historic Old Town Florence (with its amazing food and drink)! Sandboarding, sand sledding, ATV & sandrail rides, championship golf, horseback riding, a cave full of sea lions, a historic lighthouse, mushroom foraging or strolling in the petrichor of ancient forests, kite flying, or s’more-making over your fire on the beach. Each new memory will be worth every minute of a little extra drive!
Where: Florence Area Chamber of Commerce
The Estate House at Balsall Creek
Spend Time in a Stunning Space With Festive Indoor OfferingsOpens in new window
The Estate House stands within a vineyard atop Calkins Lane in the Willamette Valley, offering spectacular views of the Chehalem Mountains, surrounding vineyards, and the Dundee Hills all year long. Take in the views while cozied up by the indoor or outdoor fireplaces, and choose from three tasting experiences that each showcase at least four estate-grown varieties.
Where: 18430 NE Calkins Lane, Newberg.
Pioneer Courthouse Square
Get a Dreamy Vacation Rental for a Winter Wonderland ExperienceOpens in new window
Mount Hood rentals on vacasa.com put you where the action is—whether that's first tracks at Timberline, snowshoe treks to frozen Trillium Lake, or soaking at Bagby Hot Springs after a powder day. Vacation homes that actually deliver: forest cabins for total off-grid vibes (with Wi-Fi, obviously); riverside retreats with hot tubs overlooking the Salmon River; slope-adjacent chalets where you can see the mountain from your morning coffee; spacious lodges for the whole crew. Must-have experiences close by include: night skiing under the lights at Skibowl; snow tubing at Mt. Hood Adventure Park—family-friendly chaos without the cost of a lift ticket; snowshoeing through silent forests where your tracks are the only ones; cross-country skiing on groomed trails at Trillium Lake or Cooper Spur; fat biking on snowy forest roads for the “regular biking is boring” cyclist.
Where: Mount Hood, including Welches, Government Camp, Rhododendron, Zigzag, and Brightwood.
Rockaway Beach
Explore 7 Miles of Sandy Beach, Hiking Trails, and RestaurantsOpens in new window
Discover Oregon’s welcoming vacation destination, Rockaway Beach. Hike the accessible Old Growth Big Cedar Trail. Ride a fat-tire bike on the beach. Hop aboard the Oregon Coast Scenic Railroad. Play putt-putt golf on the Wizard of Oz course. Grab a Pronto Pup or fresh seafood dinner. There’s always something for you here.
Where: US Highway 101, Tillamook County
REX HILL
Discover the Artistry of Oregon WineOpens in new window
Every visit to REX HILL is a sensory journey you won’t find anywhere else. What sets REX HILL apart is the immersive nature of its wine experiences, each crafted to awaken your senses and warm your winter. Offerings include: Somm’s Table, where you can enjoy intimate, food-paired tastings led by expert sommeliers; and the Legacy Tour, where participants embark on a guided exploration of REX HILL’s storied vineyards and cellars. You can also make tasting reservations and cozy up in the elegant tasting room, surrounded by breathtaking valley views, and savor wines that reflect the unique terroir and spirit of Oregon. Enjoy 25% off experience reservations with the code REXESCAPE25, valid Dec. 1, 2025, through March 31, 2026.
Where: 30835 OR-99W, Newberg