Guesthouse vacation rentals in Portland

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Top-rated guesthouses in Portland

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Northeast Portland

4.95 out of 5 average rating, 521 reviews

Concordia Fir Cabin

The ultimate Portland cozy place to stay (see reviews) Proximity to great pubs, top-rated restaurants, dispensaries, coffee & tea, airport, and much more! The shopping/dining of Alberta St, Dekum St, 42nd Ave just blocks away. Queen size bed, eucalyptus hardwood floor, quality decor, turntable and extensive vinyl record collection, private yard, outdoor fire-pit, *private parking (NOTE-between June and Oct parking is not guaranteed-please ASK if needed) heating/air, coffee maker, and microwave.

Jun. 13 – 20

$161 CAD per night

Guest favourite

Guesthouse in Portland

4.98 out of 5 average rating, 113 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Sep. 18 – 25

$186 CAD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 541 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, newly constructed detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

Apr. 26 – May 3

$195 CAD per night

Guest favourite

Guesthouse in Portland

4.98 out of 5 average rating, 476 reviews

Little Cedar House High Speed WIFI - Super Clean

Two year new detached guest house in Laurelhurst/North Tabor. Bright and spacious with vaulted cedar ceilings. Modern Industrial style with many eco-friendly features such as mini-split heat/ac, tankless water heater, and all-natural fiber area rugs and linens means fewer toxins and a low carbon footprint. Situated near Laurelhurst and Mount Tabor parks with restaurants and amenities nearby. We are also pet friendly and allow well-behaved dogs on leashes for a $25 fee per dog, per visit.

Oct. 22 – 29

$251 CAD per night

Guest favourite

Guesthouse in Portland

4.99 out of 5 average rating, 155 reviews

Grant Park Guest House

Newly built guesthouse in highly desirable Grant Park. Beautiful and relaxing one level space with vaulted ceilings, exposed beams, skylights and lots of natural light. All amenities: high speed internet, washer & dryer, full kitchen, memory foam mattress, TV, and private entrance with patio and cafe set. Easy check out! Location is close to everything: great restaurants, food cart pod, Whole Foods, Trader Joe's, Grant park, airport, and more! Walk score of 94. Great space for a get away!

Sep. 24 – Oct. 1

$254 CAD per night

Guest favourite

Guesthouse in Portland

4.92 out of 5 average rating, 663 reviews

Casa Chica PDX

A mini house in the Rose City Park neighborhood of the City of Roses that will make you feel right at home. Casa Chica is full of natural light, and a short walk away from Portland-caliber coffee, a local brewery, wood-fired pizza, bagels made fresh daily, a Mom n' Pop wine shop, an independent movie theater, two beautiful parks, groceries, and the best Vietnamese food in Portland (in our opinion). Follow us on Instagram for more photos, tips, and info: @casachicapdx

Jan. 24 – 31

$163 CAD per night

Guest favourite

Guesthouse in Northeast Portland

4.95 out of 5 average rating, 281 reviews

Cozy Alley Cottage, Concordia/Alberta Arts, NE PDX

Come enjoy our beautiful detached cottage, in a Concordia alley 5 blocks from Alberta Street. French doors lead onto your own private patio. It has a fully stocked kitchen, with everything you need. The cottage is designed to be self sufficient, and full of natural light. We are a 10 minute walk to the Alberta Arts District. You can wander the alleys and visit the famous Concordia chicken coup, wander through Alberta park, to the vibrant Alberta Arts district.

Aug. 11 – 18

$183 CAD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 388 reviews

Moss Rock Retreat - Near Leach Botanical Garden!

Moss Rock Retreat is a peaceful tiny home surrounded by an acre of hillside gardens. Tucked behind the magical Leach Botanical Garden in a forested neighborhood, Moss Rock has the serenity of a mountain retreat - but is only 20 minutes from downtown and PDX. Come for respite from the busy world, a quiet workspace, a creative getaway, a romantic weekend, or to explore the natural beauty of Oregon - all are possible in the comfortable intimacy of Moss Rock Retreat.

Oct. 7 – 14

$145 CAD per night

Guest favourite

Guesthouse in Portland

4.99 out of 5 average rating, 383 reviews

Beautiful, Contemporary Farmhouse

Modern farmhouse-style guest home with a private entry in a quiet and convenient Portland neighborhood. This home was built in 2017 with simplicity and style in mind. 5 minutes to Wilshire Park. 5 minutes to the vibrant Alberta Arts district. 5 minutes to charming and friendly Beaumont Village. 5 minutes to up-and coming restaurants on 42nd Avenue. 15 minutes to the airport. 15 minutes to downtown. A pleasant and peaceful hub for all of your Portland adventures.

Sep. 13 – 20

$236 CAD per night

Guest favourite

Guesthouse in Northeast Portland

4.94 out of 5 average rating, 839 reviews

The Hen House: Private unit in NE

The Hen House is a converted garage, built from mostly salvaged material, and has everything you need for an easy visit. The loft has a queen bed but stairs are very steep so I recommend the pullout single bed downstairs if uncomfortable with steps. I'm near Mississippi area, Williams and Alberta Arts District with 2 grocery stores within walking distance. Unit stands alone and there is a garden and friendly animals to hang with outside. Dogs allowed.

Jan. 6 – 13

$146 CAD per night

Guest favourite

Guesthouse in Portland

4.97 out of 5 average rating, 131 reviews

The Perch PDX - Modern Studio on Division

A guesthouse in the SE Division/Hawthorne neighborhood that will make you feel right at home. The Perch PDX is light and bright. It's a short walk away from locally roasted coffee, farm-to-table fine dining, endless brunch options, a hip brewery and beer garden, bagels made fresh daily, authentic Mexican street tacos, a neighborhood wine bar, a fiercely independent movie theater, groceries, and some of the best Thai food in Portland.

Sep. 3 – 10

$155 CAD per night

Guest favourite

Guesthouse in Central Northeast Portland

4.91 out of 5 average rating, 327 reviews

New Classic Portland Guesthouse

Be one of the first to enjoy my beautiful, light filled, newly built 2 story, one bedroom guest house. Furnished and decorated in classic Pacific Northwest Style. Located in a separate structure from my home sharing the same lot. Private, 24 hour entry. Ideally situated halfway between the airport and downtown in NE Portland. Walking distance to views of Mt. Hood above a wooded golf course and park teeming with wildlife.

Oct. 18 – 25

$173 CAD per night