We all need a staycation or a trip to a different city from time to time. Whether you’re a Portlander feeling a little cooped up or a visitor looking for a special Bridge City experience, picking the perfect home away from home is crucial.
We went looking for unique lodgings around town that showcase that “keep Portland weird” spirit. So choose your ideal digs, pack your bags, and get ready for a memorable getaway.
Cabin fever
Eagles Nest Treehouse | Southwest Hills
Escape into a “Tarzan” fantasy at this Airbnb situated 18 ft off the ground with trees growing through the deck. Guests reach the front door by way of a suspension bridge, then can ride a zip line back down to a secluded picnic area.
My Tiny Wine Wagon | Sherwood
Find peace and privacy at this tiny home in a rural setting. Explore nearby Ponzi Historic Estate and Cooper Mountain Vineyards, or take in the natural beauty of Tualatin River National Wildlife Refuge.
Tomahawk Island Cozy Houseboat | Hayden Island
Get the cabins-in-the-woods vibe, without the woods. Soak in views of the Columbia River and explore the area by kayak during your stay at this quiet floating home.
Hideaways with history
McMenamins White Eagle Saloon & Hotel | Eliot neighborhood
Since the turn of the century, this building has been a popular local hangout for both the living and the dead. Guests and employees have reported paranormal experiences, so if you’re into haunted history, this is the place for you. But light sleepers, beware — live music on the first floor every night (and the reported ghosts) may keep you awake.
Benson Hotel | Downtown Portland
Built in 1912, this hotel features original Italian marble floors, crystal chandeliers, and the “largest collection of Circassian walnut within one building.” The 12-story building on Southwest Broadway was originally known as the New Oregon Hotel and has hosted multiple US presidents, including William Howard Taft and Barack Obama.
The Royal Scott Double Decker Bus | Russell neighborhood
Hop aboard this 1953 commuter bus from Manchester, England, that locals will remember as the former home of the Grilled Cheese Grill. It’s now a tiny home on wheels, complete with a kitchenette, artwork, composting toilet, and lounge areas.
Farm charm
Island + Alpaca Farm Retreat | Sauvie Island
Escape the hustle and bustle of everyday life with a stay at this working farm located on a wildlife refuge. Wake up to views of grazing sheep and pristine mountains, the sound of a crowing rooster, and the smell of clean, open space.
Roloff Farms | Hillsboro
You and up to 15 guests will sleep comfortably at this iconic, 5,300-sqft farmhouse that housed the Roloff Family in the “Little People Big World” series for 15+ years. Play foosball or cornhole in the converted garage, swim in the pool, watch a movie on the 80" TV, and enjoy the fresh air at this working farm.
Wilson Farm Cottage | Damascus
Experience simpler times at this 8-acre working farm with access to trails through an established filbert orchard and 100-ft-tall cedars. You’ll stay in a handcrafted cottage, enjoy a daily farm-fresh breakfast, and see animals like ducks and pigs.
Here’s the theme
Jurassic Retreat | Washougal, WA
Two words: animatronic dinosaurs. This rural rental pays homage to the “Jurassic Park” movies, from the five massive dinos that greet guests outside to faux books written by the movie’s fictional professors.
Tiny Digs Hotel | Kerns neighborhood
Experience small living in one of 12 custom-built tiny homes, each featuring a unique design — like the railroad-inspired Arthur House or the Victorian shabby chic Cottage House.
Retreats on the water
Flamingo House | Hayden Island
Let your worries float away at this cotton-candy-colored floating home on the Columbia River. Head out the door and rent a kayak or a stand-up paddle board to explore the river.
Willamette River Yacht | Milwaukie
Stay on a 55-ft yacht with three bedrooms, a living room, and an upper deck. Guests can add a private cruise to their stay for an additional fee.
The Lily Pad | Sauvie Island
Listen to local waterfowl, watch passing boats, and spot fish leaping out of the river from the vantage point of this floating home on the Multnomah Channel.
Cozy cottages
Brick House Beautiful | Laurelhurst neighborhood
Picture yourself sipping tea and reading a Jane Austen novel in this historic, Tudor-style cottage apartment that’s been featured in Better Homes and Garden Magazine.
Peaceful Garden Cottage | Mount Tabor
This quiet, airy home exudes serenity. Lounge in the hot tub, enjoy heated bathroom floors, wander through the garden, or walk to nearby Mount Tabor Park.
The Green Door PDX | Overlook neighborhood
Designed to mimic a traditional European field cottage, this guesthouse is surrounded by greenery and features vaulted ceilings, an open floor plan, and a luxury bathroom.