Sweater weather is finally here, and with cooler temperatures comes the desire to snuggle up and get cozy. While it’s nice to bunker down at home, don’t miss the opportunity for fall travel. It’s a perfect time for a memorable Oregon getaway, where crisp days and harvest colors replace the crowds of summer. Here are a few places to make the most of the season.
Family Escapes in Central Oregon and the Columbia River Gorge
For a cozy trip that the whole family will love, head to Sunriver Resort near Bend, where you’ll find loads of ways to enjoy the fall season. Grab a bike from the Bike Barn and head out to explore the resort’s 40-plus-mile network of trails, or tee off at one of four golf courses. It’s a particularly good spot for multigenerational travel, with a mix of vacation homes and traditional hotel-style rooms with fireplaces.
Also in Central Oregon, recently revamped Kah-Nee-Ta Hot Springs Resort has long been a favorite among Oregon families, thanks to its steaming hot-springs pools (including a lazy river) and its ball courts and hiking trails. Kah-Nee-Ta also makes a great base for visiting the Museum at Warm Springs, an excellent place to learn about the culture and history of the Confederated Tribes of Warm Springs.
If rugged cliffs appeal more than the high desert, try one of Hood River’s newest places to stay, Lightwell Hotel & Spa or Horsefeathers Hotel, which offers luxe condos that sleep anywhere from two to six adults plus up to two kids. Twin bedding and pack ’n’ plays are even available at no extra cost. Book a ride on Mount Hood Railroad’s Fall Train excursion or make a visit to the nearby Columbia Gorge Discovery Center & Museum for cultural and natural history.
Romantic Stays in Portland and the Willamette Valley
Get a serious head-start on a romantic getaway for just you and your beloved. For an extended date night in Portland, check into one of the plush rooms at downtown’s Heathman Hotel, followed by dinner at The Tavern Restaurant on-site, which showcases Pacific Northwest ingredients. Another option is Bistecca Woodfire Steakhouse and its sister cocktail bar, Hey Luigi, both helmed by Portland Top Chef alum Gabriel Pascuzzi. After your meal, stroll next door to the Arlene Schnitzer Concert Hall for a night with the Oregon Symphony — discounts are available for hotel guests — or cozy up with a good book or a game in the hotel’s sumptuous library.
For a wining-and-dining vacation for two, head to the Dundee Hills for a night at the Grange Estate Private Residence, one of the newest properties to open in Willamette Valley wine country. Each of the nine rooms at this rural retreat is furnished with rustic-chic decor, and all guests get free tastings at The Four Graces winery, owned by the same family. Stay for dinner at Anthology, offering a communal fine-dining experience that shows off dishes sourced from area farms and ranches.
A short drive east of the estate, The Ground is an equally great place for a romantic retreat, offering nine plush suites with private patios and Mt. Hood views. The property sits on the grounds of Tabula Rasa Farms, which provides ingredients for the inn’s included breakfasts. For dinner pop over to nearby Carlton for a meal at Hayward Restaurant, helmed by James Beard semifinalist chef Kari Shaughnessy.
Restful Retreats on the Coast and in Eastern and Southern Oregon
Fall is an equally great time for a wellness getaway with your besties or a solo-cation devoted to relaxation. If you love to read, make a beeline to Hotel Sylvia in Newport, the Oregon Coast’s own literary hotel. Formerly known as the Sylvia Beach Hotel, this beloved spot was renovated and relaunched in 2025 with a few sleek interior upgrades and the addition of a restaurant. Still, the original concept remains strong with author- and book-themed rooms and a huge library of books to borrow during your stay.
On the other side of the state, The Lodge at Hot Lake Springs in La Grande is a great place for a quiet getaway, especially if you’re a fan of history — or hot springs. Occupying a 1906 brick building that was once a sanatorium, this historic property offers simple rooms and easy access to five soaking pools fed by geothermal springs, some of which look out over Hot Lake, known as Ea-Kesh-Pa by the Nez Perce people.
Ashland’s Lithia Springs Resort is another notable place to take the waters, as they used to say. Each of the 38 rooms at this low-key hotel has its own private soaking tub with Lithia Springs water on tap, so that you can soak to your heart’s content without leaving your room. Don’t miss a massage or facial next door at the Waterstone Spa. While you’re in town, make sure to enjoy some forest bathing at nearly 100-acre Lithia Park, a superb spot to check out the fall colors.
