5 Quirky Portland, Oregon, Neighborhoods With Affordable Vacation Rentals

A summer vacation to Portland, Oregon, is a chance to lead The Good Life. You'll eat delicious food, drink excellent beer and coffee, go thrift shopping, and explore neighborhoods full of quirky stores and street art. The summer weather is near perfect, and everyone is out making up for the long, dark winter. It's the time of year to bike around with "Feel It All Around" by Washed Out playing in your head. This isn't a city full of must-see sights to check off a bucket list, but a city of good vibes, peace, and quiet pleasures. In fact, Portland is even touted as the "quietest city in America."

A visit to Rip City may also be more affordable than you'd expect. A Hotels.com report ranked Portland among the most affordable cities for four- and five-star hotels, with prices ranging from $226 to $287. That's reasonable enough – but many neighborhood stays cost even less, especially the ones listed below. To preserve housing access, Portland enforces strict rules on short-term rentals on platforms like Airbnb and Vrbo. In most cases, hosts must live on-site and rent out only rooms or attached suites. If you don't want a hotel, look out for backyard ADUs, basement suites, and studios above garages. 

I grew up here and come home often. Its neighborhoods are walkable and reward the curious. Sure, you can Uber around, but then you'd miss the painted intersections, a toy car library with a racetrack built into an old gas pump, and countless other community art installations.

Right across the Willamette River from downtown is my favorite part of the city. The Central Eastside has become a late-night hot spot, home to restaurants and breweries that help Portland punch above its weight. It's an easy walk or MAX ride over a bridge to the Westside to visit Powell's City of Books, but you may find yourself lingering here.

You'll pay a little premium to be central. The hip Jupiter Hotel has fun chalkboard doors and rooms starting at $199 per night as of this writing. Nearby, Jupiter Hotel NEXT offers city views and rooms starting at $279 a night. Just outside the Central Eastside district, on a cafe and bar-lined street, is the tiny-house hotel Tiny Digs. Here, a private house is $249 per night.

For meals, try Kann, one of the most acclaimed restaurants in the U.S. It's worth the effort to get a reservation to try Top Chef alum Gregory Gourdet's food. For a late-night tea and dessert and a taste of old-school Portland, go to Rimsky-Korsakoffee House. It's in an old Craftsman, purported to be haunted, that feels like a spooky Russian coffeehouse where students meet to discuss a Communist revolution. An old man plays piano as night owls drink coffee and eat brownie sundaes. If you're looking for a show, catch some top-rated comedy at Kickstand Comedy, which puts on packed stand-up shows in nearby Laurelhurst Park in the summer. Out late? Stop at Cartopia, one of Portland's oldest food cart pods.

Close to the airport in the Northeast quadrant (Portland has six quadrants, don't worry about it) is the Alberta Arts District. It centers on Alberta Street — a stretch lined with colorful murals and galleries. There are markers along the street detailing the history of the neighborhood's Black population. During the summer, on the last Thursday of each month, 15 blocks are closed to cars for the Alberta Art Walk, with live music, street performers, and plenty of local artists selling their works.

If you were the type to sleep in class, lean into your inclinations by staying at the funky McMenamin's Kennedy School. Splurge to stay in a converted classroom for $295 per night as of this writing. There are different bars throughout the building, a theater, and the teacher's lounge, which is now an outdoor soaking pool. If you just want something simple, this tiny home on Vrbo costs $170 a night and is right off the main street.

No Saint, just north of Alberta Street, has some of the best pizza in the city. Last year, I had a four-onion pie there that stopped the whole table mid-conversation, and we silently enjoyed each slice. Back on Alberta Street, you can stop at one of the best breweries in the country, Great Notion, known for hazy IPAs and inventive sours. A few blocks down is Proud Mary Coffee, where, with your Aussie-style breakfast, you can get high-quality drinks like a rare and delicious gesha pour-over or a well-crafted flat white because Portlanders know good coffee. Portland is the coffee capital of the U.S., after all.

On the edge of North Portland, but not too far from downtown and the rest of the Eastside, is the Mississippi neighborhood. Running along Mississippi Avenue, it's a busy neighborhood for late-night goers hitting the bars before or after a show at Mississippi Studios. The venue is known for having excellent acoustics, so a concert there is always good.

It's less of a tourist spot, and there are no hotels, so lodging in the neighborhood is a little more sparse. Thankfully, Vrbo has some good options. This colorful, $110-a-night tiny home with unique furnishings has a front porch facing an art installation in the alleyway, so you can be fully immersed in the funky vibes. This cozy apartment is set back in a garden and just two blocks from the main street at $195 a night, allowing you to have a quiet place to rest in the middle of the action. 

Walking along the avenue, your eyes will be drawn to Paxton Gate. If you're into taxidermy, bugs, or skulls, you've found your store. Across the street is a food cart pod attached to the German beer garden, Prost. Among the many great food carts to choose from, DesiPDX stands out for its fresh, flavorful food. If you're looking for pizza, Lovely's 50/50, of "Chef's Table" fame, offers seasonal, creative pies. Make a reservation for Eem at nearby Williams for Thai BBQ, like the white curry with burnt ends.

Over on the Westside, on the edge of the immense Washington Park and Forest Park, is the dense Northwest — often called Nob Hill — neighborhood. It's in the Northwest quadrant, but the Northwest neighborhood is specifically the area along NW 23rd Avenue. One of the most walkable neighborhoods, it is a grid of old Victorian homes and brick apartment buildings. The greenery creeping over sidewalks and porches is a reminder that, while you are in the city, the woods are close.

The centrally located Portland International Guesthouse is a European-style inn with nice rooms and shared bathrooms starting at $85 a night. It's right by cafes and bakeries, and less than a 15-minute walk to the light rail. If shared bathrooms aren't your thing, you can stay in a modern tiny home near the neighborhood at the modern Slabtown Village, starting at $217 per night as of this writing. 

One of my favorite ways to spend a day is to take the MAX to the Zoo stop to hike some of the 70 miles of trails in the dense woods. As I wander back down to the city, I'll stop at the International Rose Test Garden or Portland Japanese Garden, which was named one of the most beautiful gardens in the world by Homes & Gardens. At the end of the hike, I hit the neighborhood to grab a high-quality slice from Scottie's Pizza Parlor. If I'm not done walking, I'll go a little further to nearby Slabtown for a beer at the many-award-winning Breakside Brewery.

Division Street is the epicenter of the Division/Clinton neighborhood. You can stay at the Evermore or Bluebird Guesthouses. The two beautiful old homes, now boutique hotels, make you feel like you live in Portland. They give you easy access to everything great in the neighborhood. Bluebird has rooms starting at $156, and Evermore starts at $205 as of this writing.

The neighborhood is known for its artsy theaters. The fiercely weird Clinton Street Theater is home to obscure movie screenings, X-Files burlesque shows, and a regular showing of "The Rocky Horror Picture Show." The Tomorrow Theater, operated by the Portland Art Museum's nonprofit arm, programs arthouse films and experiential events. Before a screening of "Belladonna of Sadness," a wellness expert led us through a "bodyroll session" to ground us in our bodies.

Portland is widely considered one of the most sex-positive cities in America, and you can get a glimpse with a visit to the empowerment- and education-focused adult toy store, She Bop. For meals, Division has plenty to eat, especially if you like sweets. Lauretta Jean's makes incredible pie — the custardy salted honey is my personal favorite. Down the street, Pinolo Gelato stands out in the ice cream-hungry city where Salt and Straw was born. The gelatos highlight the famed seasonal bounty of the nearby Willamette Valley. If you're like me, you'll eventually need to eat something healthy after a stretch of overindulgence. The Garden Monsters food cart serves up tasty, filling salads. Don't worry, the food cart pod it's in has a beer bar.