Portland staycations can be as active or as laid-back as you want them to be, but they’re always a ton of fun. Here are our top picks for the best hotels, quirky Airbnbs, and cozy Vrbos to plan your next staycation in Portland, Oregon.
Canopy by Hilton Portland Pearl District
Canopy by Hilton Portland Pearl District makes a wonderful staycation because of its location in the city, on-site restaurant, rooftop fitness center, and bar. One of the top hotels near Portland’s Pearl District, you’ll be among the art and nightlife scenes and have easy access to complimentary bikes, a waterfront trail, and downtown. Guests here get free Wi-Fi, business center access, and pet-friendly rooms made even better with a pet gift bag. In total, there are 153 guest rooms here and four meeting rooms.
Casa Maggie Mae
Staycations are fun and convenient when you stay at this VRBO property that’s a house measuring 1,700 square feet in size. It sleeps six people and has two bedrooms and 1.5 baths. It’s an ideal staycation spot because of the fast internet, comfortable spaces for adults and children, and central location in trendy NE Portland. There’s free street parking, and North Mississippi and the Alberta Arts District are less than a mile away. You’ll also get an inviting kitchen, complimentary toiletries, hardwood floors, a furnished private patio, and a community pool when you stay here for two nights or longer.
Eco Tiny Cabin by Mississippi/N. Williams Ave.
This tiny cabin is a popular staycation that accommodates two guests with one bedroom and one bath. It’s in a great location where you can access public transit, rental bikes, and locally-owned restaurants and shops. The cabin is 220 square feet in size and made with sustainable wood and vintage fixtures. Perks are the well-appointed shower, mini-fridge, coffee and tea supplies, and large windows that overlook the yard. The covered back patio is shared with the main house, and there is no kitchen here.
Henriette House
Henriette House is clean and cozy for your staycation experience and accommodates up to six guests with two bedrooms and two baths. It’s an Airbnb property and 1907 craftsman home in a hip neighborhood. This LGBTQ-friendly spot has lots of comfy places to hang out, board games, a fenced back yard, and patio area. It follows strict cleaning and sanitizing guidelines and is within walking distance to bars, restaurants, and food trucks. You’ll have access to the entire house except for the basement. Laundry is available onsite upon request so the host can give you access to it.
McMenamins Crystal Hotel
A popular pet-friendly hotel in Portland, Crystal Hotel is also a top staycation spot in its century-old flatiron classic building with stylish rooms. Zeus Café is the restaurant on the first floor that serves all meals using Northwest ingredients. There’s a saltwater soaking pool at the hotel, as well as a music venue called Al’s Den. Best of all, there are some pet-friendly rooms here so you can bring your pup along for the staycation.
Zen Cottage in NE Alberta Arts Area
Plan a staycation at this cottage in the Beaumont-Wilshire area and enjoy 800 square feet of Zen all to yourselves. This space sleeps four people and has one bedroom and one bathroom. There is a six-night minimum stay here, which makes it ideal for a longer vacation close to home. The cottage is in a separate part of the owner’s large grounds and has a private fenced area and entry. There’s street parking right outside, and the host is adhering to strict cleanliness protocols of the space. You’ll also get a washer and dryer and fully equipped new kitchen here.
Sleek Townhome with Patio
We also love this 2,016-square-foot townhome listed on VRBO for a staycation because of it’s great patio and easy walking distance to breweries, trails, and restaurants. It sleeps six people and has two bedrooms and 2.5 baths. It’s just a couple blocks from Breakside Brewery and has central air conditioning. The second floor has ping pong and pool tables, hiking trails are just one mile west of here, and the home is equipped with smart home technology that monitors noise levels to be respectful of neighbors. Therefore, this is a good staycation spot for peace and quiet!
The Hoxton, Portland
There are comfy rooms at The Hoxton, Portland, which is a staycation destination with all-day dining, a cocktail bar, and location in the heart of the historic Old Town Chinatown. Lovely Rita, Tope, and 2NW5 are the onsite dining and drinking establishments. When you stay here, it’s easy to get on a bus or the MAX to get around or take a hike around Forest Park. The PDX Airport is about a 20-minute taxi ride away, and the closest MAX station is a three-minute walk.
Peaceful Garden Cottage, Close to Mt. Tabor Park
Here’s a 650-square-foot cottage that’s listed on VRBO and sleeps up to four people. It has one bedroom, one bathroom, and a three-night minimum stay. It’s about 10 minutes from downtown and at the base of Mt. Tabor Park. When you stay here, you’ll get a fully equipped kitchen, washer and dryer, covered porch that overlooks the garden, and a spacious living room. Pets are not allowed in this private apartment.
McMenamins Kennedy School Hotel
Another great McMennamins option is the Kennedy School, which has spacious rooms with private baths. It is a historic elementary school that dates back to 1915 and has been renovated into a unique Portland hotel. Some rooms even have the original chalkboards and cloakrooms! Other onsite perks are the small bars, soaking pool, movie theater, gift shop, and brewery. The onsite restaurant here has plenty of outdoor seating for your staycation adventure here. Pets are allowed for a $15 fee.
Zen Loft
Another good option for two people on a staycation is this guest suite that’s on Portland’s popular Division and Hawthorne streets and off SE Restaurant Row. It is a large two-car garage that was converted into an industrial living space and filled with handmade cabinets, bar stools, artwork, and other features. It’s sleek and simple and a great pick for guests who enjoy cooking. You can use the outdoor patio, fireplace, and hot tub when you stay here. Parties and events are not allowed without prior approval. Other perks are Wi-Fi, free parking on the premises, and being in a truly fantastic neighborhood.
Magic Barn
The Magic Barn is one of the most talked-about Airbnbs in all of Portland. This is a staycation guesthouse that can accommodate up to 10 people and is a former sculpture studio decorated with upcycled furnishings and located three blocks from the boutique district of SE Hawthorne and Division. This is a staycation spot that practices social distancing and has a full kitchenette, clawfoot tub, and sleeping options for couples or larger families. Upon request, there are also baby amenities offered. Your hosts make public art bronze sculpture monuments professionally, and there’s a professional writer living on the property as your onsite host.
