15 Charming Small Towns in Oregon

When you hear “windsurfing capital of the world,” what springs to mind? Probably some breezy destination in California or the Caribbean. Well, it’s actually Hood River! If windsurfing doesn’t float your boat (sorry, we couldn’t resist), rest assured that Mount Hood provides countless opportunities for hiking, biking and skiing. There’s also fishing and kayaking on the Columbia River.

Where to stay:

• Remodeled House (4 guests): $169/night
• Mountain Home (6 guests): $217/night
• Home in the Hills (8 guests): $310/night

The state with the most ghost towns? Oregon! And Sumpter is perhaps the most intriguing of the bunch. Platted in 1898, this former gold mining hub showcases many reminders of the past—abandoned churches, saloons, newspapers, and an opera house. True to its Wild West roots, adventure awaits around every corner. As the gateway to the Blue Mountains, Sumpter also puts travelers in proximity to rugged trails.

Where to stay:

• Mobile Home (6 guests): $120/night
• The George House (10 guests): $212/night
• Good Bear Ranch House Retreat (20 guests): $342/night

One of the most photographed towns in the whole of the Pacific Northwest, Cannon Beach boasts scenery so stunning it’s hard to describe in words. (But we’ll give it a shot.) Expect a craggy coastline punctuated by the morning mist, secluded coves, tidal pools and lighthouses. You don’t have to be a shutterbug to appreciate the art galleries, boutiques, and distilleries.

Where to stay:

• Oceanfront House (5 guests): $860/night
• Historic Cottage (8 guests): $245/night
• Charming Home (8 guests): $263/night

Yachats (pronounced Yah-hots) comes from the Chinook word Yahut, which means “dark water at the foot of the mountain"—an accurate way to describe this coastal enclave that’s wedged in between the splendor of Devil's Churn and Thor's Well. The town of Yachats itself has numerous galleries displaying Native American works of art, gift shops and seafood restaurants. Nearby Cape Perpetua is a bucket-list hike.

Where to stay:

• Ocean Bay Cottage (4 guests): $200/night
• The Overlook (8 guests): $179/night
• Luxury Oceanview Home (10 guests): $375/night

Nestled in the heart of Willamette Valley, McMinnville is dotted with coffee shops, farm-to-table restaurants and tasting rooms. Of course, you’ll also want to venture beyond the main drag to one of the many family-run wineries that produce some of the best Pinot noir outside of Burgundy. For a hit of cosmopolitan panache, check out the ultra-chic Atticus Hotel.

Where to stay:

• Downtown McMinnville Cottage (4 guests): $150/night
• Charming Bungalow (4 guests): $195/night
• Luxury Loft (4 guests): $294/night

Where can you see ranch hands wearing wide-brimmed hats, accomplished trekkers just back from conquering a snow-capped peak, artists in paint-splattered overalls and wide-eyed tourists strolling the same cobblestone sidewalks? Joseph. This small town in northeast Oregon turns on the charm in a big way. It’s rugged, down-to-earth, hip and artsy all at the same time. There’s just no place quite like it.

Where to stay:

• Charming Cottage (4 guests): $235/night
• The Wild Iris House (6 guests): $150/night
• Newly Remodeled 1930s Charmer (6 guests): $255/night

Far away from the hustle and bustle of big-city living, the quaint coastal town of Gearhart doesn't even have traffic lights. What you will find are antique shops, local spots to buy home goods, an art gallery as well as James Beard-approved restaurants that serve Pacific Northwest seafood staples like local Dungeness crab, salmon, oysters and mussels.

Where to stay:

• Beachfront Condo (6 guests): $133/night
• Comfort by the Coast (6 guests): $439/night
• Classic Beach House (12 guests): $627/night

Bet you didn’t know that Astoria holds the title of oldest settlement west of the Rockies. Victorian-era homes and museums recall the history of this centuries-old fishing village, while innovative breweries add a modern touch to the mix. Since Astoria is perched on the Columbia River, just a few miles from the Pacific Ocean, visitors can take advantage of everything from stand-up paddleboarding to coho fishing.

Where to stay:

• Waterfront Condo (2 guests): $279/night
• Comfy Apartment (4 guests): $163/night
• Remodeled 1926 Home (5 guests): $258/night

Don’t let the name confuse you, Baker City is a small town that's steeped in history. An old-school trading post set along the Oregon Train (yes, the real thing that inspired the popular computer game), this eastern Oregon gem lures tourists with its Victorian-era buildings, indie shops and museums. No trip to Baker City would be complete without a visit to the National Historic Oregon Trail Interpretive Center.

Where to stay:

• Charming Downtown Loft (4 guests): $131/night
• Turn of the Century Charm (6 guests): $150/night
• Michelle's MCM (8 guests): $163/night

Situated at the mouth of the Siuslaw River Florence has more scenic sights than residents (OK, not literally, but you get the picture). So it’s no wonder this coastal idyll lures nature lovers and adventurers. On the mile-long list of outdoor attractions? The Sea Lion Cave, expansive sand dunes and the hiking trails leading to Heceta Head Lighthouse. With any luck, you might even spy gray whales.

Where to stay:

• Oceanfront Cottage (2 guests): $139/night
• Little Beach Bungalow (4 guests): $165/night
• The Dunes Condo (4 guests): $195/night

The eastern gateway to the Columbia River Gorge National Scenic Area, The Dalles is one of those rare places that impresses on every level. It’s an epic home base for hiking, biking and fishing. The past is very much alive thanks to the many museums and murals that cover the landmark downtown buildings while wineries give visitors a chance to savor local sips.

Where to stay:

• Modern Home (6 guests): $292/night
• Beachfront Rental House (6 guests): $492/night
• Classic Home (8 guests): $509/night

Placer gold was found in Jackson Creek back in the 1850s. And so begins the gilded legacy of Jacksonville. Today, this 19th-century mining town flaunts more than 100 buildings on the National Register of Historic Places, including enchanting Victorian-era homes. Tasting rooms, boutiques, homestyle restaurants and live music number among the enticing modern attributes.

Where to stay:

• Charlene's Cottage (3 guests): $110/night
• Historic Bradshaw House (4 guests): $158/night
• Beautiful Luxury Cottage (6 guests): $195/night

Established in 1854, Silverton literally popped up, err was planned, around a large white oak tree. This imposing natural landmark has long served as a meeting point for Native Americans and, more recently, tourists looking to snap photos. Adding to the list of must-see attractions? A sprawling 80-acre botanical garden with gorgeous blooms and Silver Falls State Park.

Where to stay:

• The Silverton Cottage (4 guests): $120/night
• Comfortable Farmhouse (7 guests): $135/night
• Historic Silverton Home (10 guests): $417/night

It’s downright impossible not to fall for Sisters. Framed by a trio of peaks to the west, this mountain town will steal your heart with its fresh alpine air, laid-back pace and creative spirit. Other reasons we’re sweet on Sisters include excellent biking, hiking and skiing. Did we mention it’s home to America's first beer spa? Name a more only-in-Oregon activity. Seriously.

Where to stay:

• Cozy Downtown Condo (4 guests): $166/night
• New Build (4 guests): $190/night
• Two-Bedroom Rental (4 guests): $194/night

With fewer than 2,000 residents, Brownsville definitely falls into the category of a small town. Population size aside, this quaint community in the foothills of the Cascade Mountains—which you might recognize as Castle Rock from the 1986 flick Stand by Me—feels frozen in time. Strolling the streets of downtown, it could easily be 1921 or 2021. Don’t forget to visit The Moyer House.

Where to stay:

• Farmhouse Right Off of I-5 (4 guests): $150/night
• Cute and Comfy House (7 guests): $175/night
• Apartment Above Wine Shop (12 guests): $307/night