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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.

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Canopy by Hilton Portland Pearl District Canopy by Hilton Portland Pearl District
Canopy by Hilton Portland Pearl District

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 Casa Maggie May interior
Credit: VRBO.com
Casa Maggie May interior

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. Eco Tiny Cabin yard
Credit: Airbnb.com
Eco Tiny Cabin yard

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 Living space in Henriette House
Credit: airbnb.com
Living space in Henriette House

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 Crystal Hotel
Credit: mcmenamins.com
Crystal Hotel

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.

Garden Oasis Guest House Garden Oasis Guest House, Airbnb in Portland, OR
Credit: airbnb.com
Garden Oasis Guest House, Airbnb in Portland, OR

Garden Oasis Guest House

This popular Airbnb property is a tiny house in a garden setting that has a kitchenette. It is great for two guests and has one bed and one bath. Guests also love the private patio, hammock, and having access to Wi-Fi, TV options, and a gas BBQ. The patio is private but the garden and BBQ are shared. The Airbnb is close to the Alberta Arts District and Mississippi Avenue so you can experience the area. For your staycation here, you’ll be along two bus lines, have safe street parking, and also have rental bikes available a few blocks away.

Zen Cottage in NE Alberta Arts Area Bedroom in Zen Cottage
Credit: VRBO.com
Bedroom in Zen Cottage

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.

Rustic Tiny Home with Sleeping Loft in Hip Woodlawn Rustic Tiny Home, Airbnb in Portland, OR
Credit: airbnb.com
Rustic Tiny Home, Airbnb in Portland, OR

Rustic Tiny Home with Sleeping Loft in Hip Woodlawn

You’ll have this whole tiny house to yourself in Portland when you book this Airbnb property. It works well for two guests and has one bedroom for your staycation. The space was originally a Model T garage in 1926 and sits behind a 1915 bungalow. In this area are urban farms with hens, yoga, coffee shops, and restaurants. You’ll also be a block from Woodlawn Park here, so there is plenty to do in the area while still being in a peaceful place. There is no bathroom in this tiny house so you’ll be given a key to the main house about 20 feet away. Pets are welcome with host approval and a fee. Amenities here include a kitchen, Wi-Fi, and a laptop-friendly workspace.

Sleek Townhome with Patio Sleek Townhome with Patio
Credit: VRBO.com
Sleek Townhome with Patio

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 The Hoxton, Portland
Credit: thehoxton.com
The Hoxton, Portland

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 Exterior of Peaceful Garden Cottage
Credit: VRBO.com
Exterior of Peaceful Garden Cottage

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 McMenamins Kennedy School Hotel
Credit: mcmenamins.com
McMenamins Kennedy School Hotel

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 Zen Loft, Airbnb in Portland, OR
Credit: airbnb.com
Zen Loft, Airbnb in Portland, OR

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.

Super Clean Artist Loft Super Clean Artist Loft
Credit: airbnb.com
Super Clean Artist Loft

Super Clean Artist Loft

You can have this entire house to yourselves for your Portland staycation with its one bedroom and one bath. This is a clean and sanitized space in a remodeled 1910 loft that’s decorated with local art. It has a new kitchen, is across from Alberta Park, and just two blocks from the Alberta walking street. The house is in the host’s backyard, and you get private use of the outside patio and a private parking spot. There’s also a shared new hot tub here to use. Pets are not allowed here due to allergies. There is 24-hour video surveillance for your safety.

Magic Barn Magic Barn
Credit: Airbnb.com
Magic Barn

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.

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