Whether you’re looking to visit Portland in style for the weekend or are a local in need of an unforgettable staycation, we’ve compiled a list featuring 15 extraordinary rentals in Portland that are worthy of a trip for you, your partner, the bestie, or the whole squad this year.
Just a heads up: Prices may vary depending on dates selected, taxes, and booking and cleaning fees (sorry, Airbnb and Vrbo make the rules, we just follow them).
Cabin vibes
Eagles Nest Tree House
Cross the suspension bridge to this West Hills house among the forest canopy, complete with a hot tub, zip line, and loft net TV space.
- ~$192 a night
- 2 BD | 1.5 BA
- Dedicated workspace, self check-in, pets allowed, free parking
Tomahawk Island Cozy Houseboat
Why stay in a cabin by the water when you can stay in a cabin on the water?
- ~$126 a night
- 1 BD | 1 BA
- Dedicated workspace, WiFi, pets allowed, free parking, washer/dryer, air conditioning
Birch Trail Retreat
Explore the nature paths in the nearby wooded area or curl up with a good book on the lounge.
- ~$103 a night
- 3 BD | 1.5 BA
- Kitchen, indoor fireplace, pets allowed, dedicated workspace
Make it modern
Harmony House
The luxurious guest house was featured on the Portland Build Small Live Large ADU Tour.
- $116 a night
- 2 BD | 2 BA
- Parking space, high ceilings, kitchen, washer/dryer, queen beds
Midcentury Modern Nest
You’ll be just steps from the “restaurant rows” of both Williams and Mississippi avenues.
- ~$272 a night
- 1 BD | 1 BA
- Free parking, washer/dryer, WiFi
Wald House PDX
This architectural gem was featured in Dwell.
- ~$300 a night
- 2 BD | 1.5 BA
- Forest view, dedicated workspace, air conditioning, parking, security cameras on premises
Keep Portland weird
Bold Bungalow/House of Sarcasm
Creativity exudes from every nook and cranny.
- $150 a night
- 2 BD | 1 BA
- Art studio, band room, dedicated workspace, reading nook fireplace, fenced-in backyard
The Royal Scott Double Decker Bus
Catch some Zs in the two-tiered transport that once carried commuters in Manchester, England, and also housed The Grilled Cheese Grill.
- ~$117 a night
- 1 BD | 1 BA
- Private, fully-fenced backyard with patio, refrigerator, microwave, HDTV with streaming
Tibbetts Coop
Spend some time on this urban farm, which is also conveniently located near Southeast Division Street restaurants and other attractions.
- ~$98 a night
- 2 BD | 1 BA
- Luggage dropoff allowed, WiFi, central air conditioning, private patio
Call it cozy
The Lone Cedar House
Take a short walk to watch the sunset at Mocks Crest or Overlook Park while you stay at this fully detached ADU in North Portland.
- $71 a night
- 1 BD | 1 BA
- Private entrance, back patio area, great sunlight, walking distance to Portland bluffs
Handbuilt Alberta Arts Cottage
Staycations don’t get better than one booked at this self-proclaimed “biggest little house on the block” featured in The New York Times.
- $205 a night
- 1 BD | 1 BA
- Pet friendly, king-sized bed, chef’s kitchen, wood stove
Garden Tiny House
When it comes to enjoying the Woodstock neighborhood, 200 sqft is all you need.
- ~$73 a night
- 1 BD | 1 BA
- Luggage drop-off allowed, free parking, window air conditioning
Bring the whole family
You’ll find works from artist Todji Kurtzman around the house.
Photo via Airbnb
The Magic House
Sprinkle some pixie dust on your next get-together by hosting it at this spacious former sculpture studio three blocks from Hawthorne and Division.
- ~$204 a night
- 9 BD | 4 BA
- Self check-in, security cameras on premises, pets allowed, free parking
Vibrant Boho
Located only three blocks from Mt. Tabor Park, this airy home wows with its modern bohemian decor.
- ~$285 a night
- 6 BD | 3.5 BA
- Dedicated workspace, pets allowed, security cameras on premises, washer/dryer, driveway parking (two spaces)
Whismical House
From the vibrant sun gable design to the mismatched patterns on the stairs, your group will love this home’s character.
- ~$609 a night
- 9 BD | 4 BA
- Linens provided, washer/dryer, WiFi, games for kids, travel crib
