Guest house holiday rentals in Portland

Guest house in Southwest Portland

A large window offers stunning views of the valley and Mt. Hood in the distance. A cozy seating area features a colorful couch with patterned cushions, complemented by a simple wooden table. Natural light fills the space, enhancing the inviting ambiance.

4.99 out of 5 average rating, 161 reviews

Studio - Mt. Hood VIEW - Access to Trails, OHSU

The Studio is perched in the southwest hills of Portland with an amazing view of Mt. Hood and the valley below. It requires a walk up 43 stairs to access but is worth every step. The Studio was built as a workspace for a local artist and provides an amazing view of Mt. Hood. Since converted to an escape from the normal urban confines of Portland. Easy access to downtown and walking distance to OHSU and the Veterans Hospital, it provides escape and accessibility. Did we mention the sunrise view!

An open living space is equipped with a modern kitchen featuring white cabinetry and stainless-steel appliances. A spacious bed is positioned nearby, with natural light illuminating the area. A small dining bar with stools creates a welcoming space for meals or casual gatherings.

4.99 out of 5 average rating, 151 reviews

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

*We offer a 15% weekly stay discount and 20% monthly stay discount. *Photos of all businesses in this listing are < 1.0 mile away. *All Races, Gender Identities, Sexual Orientations, Religions Welcome. Our family welcomes you to a slice of our Portland life. We live in a quiet residential neighborhood where the sounds you are most likely to encounter are the distant squawks of our backyard chickens, the pitter-patter of raindrops on the skylight, or the occasional children's squeal or dog bark.

5 out of 5 average rating, 274 reviews

Clinton St Guesthouse • Walkable & Artistic

Stylish Clinton St guesthouse steps from cafés, bakeries, and transit. Features unique hand-painted floors, local Portland art (including child artists), and a small library of Portland authors. Queen bed, blackout shades, AC, desk, fast Wi-Fi, washer/dryer, and a coffee station with Moccamaster, grinder, AeroPress, French press, pour-over, and local beans. Walk to OK Chicken, Salt & Straw, Loretta Jean’s, Cookies, New Cascadia (gf bakery) Oma’s Hideaway, Cibo, Someday, The End, and food carts.

The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.

4.98 out of 5 average rating, 262 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.

The exterior of the home is highlighted by contemporary design elements and a clean white facade. A flowering tree adds a touch of color, while large glass doors invite natural light into the living area. Surrounding landscaping is thoughtfully arranged with minimalistic plantings.

4.99 out of 5 average rating, 563 reviews

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

A light-filled living area features two armchairs positioned beside large windows, showcasing views of surrounding greenery. A plush sofa offers a comfortable seating option, while a small, decorative table holds a plant. A television is mounted on the wall, enhancing the modern design.

5 out of 5 average rating, 109 reviews

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

4.98 out of 5 average rating, 120 reviews

WanderLuxe, Luxury+ Location +Walk to Food & Parks

WanderLuxe is a new, chic, guesthouse custom designed and built with you in mind. Want for nothing as you explore Portland with ease from your conveniently located home base. Walk a block to Wilshire Park for a picnic or a jog, catch a movie at McMenamins Kennedy School, eat at one of the dozens of neighborhood restaurants, or be just about anywhere in Portland in 15 minutes by car. Perfect for a romantic getaway, work trip, girls/guys trip, or just some much needed alone time.

The cottage exterior is nestled within lush greenery, featuring a textured, light-colored stucco façade and a distinctive triangular roof. Surrounding plants and stones create a serene landscape, complemented by wooden steps leading to the entrance, enhancing the inviting and private atmosphere.

4.97 out of 5 average rating, 455 reviews

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Collection, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

An open layout features a kitchen with a central island and two chairs, complemented by stainless steel appliances. Natural light streams through a window overlooking greenery. A spiral staircase leads to the loft bedroom, while polished wooden flooring enhances the inviting ambiance.

4.96 out of 5 average rating, 162 reviews

The Loft in Hawthorne Tabor

Loft style guest house with private entrance & private porch in a quiet and convenient Hawthorne Tabor neighborhood. Location: Explore the many restaurants, bars, boutiques, etc in less than 10 min walk along SE Hawthorne Blvd including: Por Que No?, Tabor Bread, New Seasons, Farmhouse Kitchen Escape to the tranquility of Mt Tabor park & trails after an enjoyable 20 min walk through West Tabor neighborhood 15 min drive to PDX Airport 15 min drive to Downtown

A modern garden retreat with sleek black exterior features a welcoming entrance framed by natural greenery. Concrete pathways lead to a patio area with seating, and large windows invite light into the space. The surrounding wooden fence provides privacy in a serene outdoor setting.

4.99 out of 5 average rating, 409 reviews

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

A warm sleeping area features a spacious bed framed by two wooden nightstands with lamps. A bright yellow throw blanket lays across the bed. The walls are painted a deep teal, and natural light enters through a window with a beige shade. A decorative piece on the wall adds character.

4.99 out of 5 average rating, 492 reviews

Cozy, Stylish Bungalow w/ Fireplace & Full Kitchen

Enjoy a comfy retreat in this cozy and bright studio with a private bathroom, air conditioning, fireplace, full kitchen and work desk. Conveniently located within walking distance to local restaurants, coffee shops, retail stores, and parks. Centrally located in Portland and just 3 miles from downtown. Take a stroll through Historic Irvington and enjoy some of the most beautiful homes and old growth trees that Portland has to offer.

A bright bedroom features a spacious bed adorned with soft linens and a light-colored throw. Two bedside tables with lamps flank the bed. Large windows allow natural light to fill the room, with a calming piece of artwork displayed on the wall.

4.97 out of 5 average rating, 235 reviews

Dreamy Modern Overlook ADU

*25% off 30 days or more until May 1st* Come experience our little piece of Portland paradise! Make yourselves at home in our guesthouse, designed to feel like your home away from home. We take hosting seriously and as longtime airbnb guests ourselves, we hope to have learned a thing or two about what makes for a comfortable stay. Expect to find a spotless place with everything you need - just like home, minus the clutter!

Popular amenities for guest house rentals in Portland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A bright studio apartment features an open layout with a lofted sleeping area. The kitchen is equipped with modern appliances and a dining table, while a comfortable sofa invites relaxation. Natural wood flooring complements the vibrant green walls, with a sturdy ladder leading to the loft.

4.96 out of 5 average rating, 267 reviews

Piedmont Carriage House - Close in NE Portland

4.96 out of 5 average rating, 112 reviews

A spacious living area features a large gas fireplace and a mounted television. Comfortable seating includes a plush couch and two accent chairs. Natural light enters through nearby windows, illuminating a casual dining table. Decorative elements provide a cozy yet modern ambiance.

Guest house in Woodstock

Family Friendly SE Portland Getaway w/2 Bedrooms

A welcoming entrance is framed by wooden siding and a covered porch. Potted plants are positioned on either side of the dark grey door, which features a modern handle. The pathway leading away from the door is visible, bordered by greenery.

4.95 out of 5 average rating, 516 reviews

The Tiny Big Guest House

A warm and inviting studio space features a spacious bed layered with soft linens. Skylights bring in natural light, enhancing the wooden walls and tiled floor. A small dining table with yellow chairs is positioned nearby, alongside a lamp and decorative elements enhancing the cozy ambiance.

4.93 out of 5 average rating, 384 reviews

Treetop Cedar Studio

A cozy sitting area is featured, with a light-colored sofa adorned with patterned cushions. A wooden coffee table sits in front of the sofa, and natural light fills the space through a window flanked by sheer curtains. A floor lamp stands beside the sofa.

4.91 out of 5 average rating, 869 reviews

Modern Garden Studio Self Check & Private Entrance

A cozy bedroom features a spacious bed adorned with a patterned duvet and decorative pillows. A flat-screen TV is mounted on the wall, while a small dining table with two chairs is positioned nearby. Natural light filters in through the windows, highlighting the wooden floors.

4.96 out of 5 average rating, 552 reviews

Newly built studio in perfect SE location

A bright interior space is designed with a kitchenette featuring green cabinetry and modern appliances. A cozy seating area includes a woven chair next to a wooden table. A colorful floral artwork adds a decorative touch to the room, enhancing its welcoming atmosphere.

4.96 out of 5 average rating, 142 reviews

Private guesthouse

A private outdoor area features a combination of gravel and stone pathways. The exterior showcases warm wood siding, highlighted by vibrant yellow trim around a large red door. Lush greenery and tall grasses add a natural touch, while a covered seating area is visible in the background.

4.95 out of 5 average rating, 636 reviews

Concordia Fir Cabin

Guest house rentals with a patio

The living room features a comfortable gray sofa flanked by light-colored lamps on side tables. A coffee table is centered on a soft rug, with a striped chair visible nearby. Large windows provide natural light, facing a well-maintained hedge outside.

4.98 out of 5 average rating, 131 reviews

The Lily Pad is a place to come and relax.

Guest house in Southwest Portland

A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.

4.94 out of 5 average rating, 154 reviews

Brand New Tiny Home/Pottery Studio in Cute Village

A cozy studio space is depicted, showcasing a comfortable seating area with a neutral-toned sofa. An open kitchen with bar seating is visible in the background, alongside large glass doors leading to a fenced backyard. A television stands against the wall, ready for entertainment.

4.96 out of 5 average rating, 258 reviews

Bright, Private & Cozy with Yard

A welcoming entrance features a white door beneath a cream-colored awning, surrounded by blue siding. Two bistro chairs with woven seats and a small table are positioned on a wooden deck adorned with string lights. Green plants add a lively touch to the space.

4.99 out of 5 average rating, 142 reviews

Garden Home Getaway

A detached entrance is seen with a wooden door and large windows, framed by a clean gray exterior. A small patio area features a table and two chairs, inviting relaxation. The surrounding landscape includes gravel and low-maintenance plants, enhancing a sense of privacy.

5 out of 5 average rating, 114 reviews

Private urban retreat, new build, 1bedroom, sleep4

A spacious living area showcases a comfortable couch accompanied by a stylish armchair. A round coffee table sits in front, and a colorful area rug adds warmth. The kitchenette is visible in the background, complemented by light wood accents and modern appliances.

4.87 out of 5 average rating, 119 reviews

Guesthouse with Fenced Yard in NE Portland

4.97 out of 5 average rating, 172 reviews

An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.

Guest house in West Linn

Charming one bedroom apartment in the forest.

4.97 out of 5 average rating, 278 reviews

A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.

Guest house in Clackamas

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Guest house rentals with a washing machine and dryer

A comfortable living area features a light-colored leather couch adorned with various textured pillows. A rustic wooden coffee table sits in front, decorated with a floral arrangement. A patterned artwork and a framed photograph decorate the walls, enhancing the stylish ambiance.

4.94 out of 5 average rating, 165 reviews

Pet Friendly, Cozy & Curated Designer Guesthouse

A cozy sitting area is furnished with patterned armchairs and a small table, providing a welcoming space. A television is mounted on the wall beneath a window, which allows natural light to brighten the room. A bookshelf displays various books and decorative items.

4.98 out of 5 average rating, 450 reviews

Maple Cottage PDX/ Fun Historic Mississippi Ave.

The open kitchen and living area feature vaulted ceilings and natural light. A fully equipped kitchen is highlighted by wood cabinetry, a gas stove, and a breakfast counter with three bar stools. Subtle green accents decorate the walls, complemented by modern furnishings.

4.82 out of 5 average rating, 190 reviews

Private Oasis! Cozy & Close to Everything!

A modern kitchen area is illuminated by natural light from a large window, highlighting white cabinetry and stainless steel appliances. A wooden dining table with chairs is positioned nearby, surrounded by soft colors and a decorative rug, creating a welcoming space for meals.

4.98 out of 5 average rating, 441 reviews

‘Well Rested’-Accessible & bright private studio

A modern yellow carriage house is set in a park-like backyard, surrounded by greenery. The structure features a second floor balcony with outdoor seating, and stairs leading down to a landscaped yard. Mature Douglas Fir trees provide shade, while a garage is located below.

5 out of 5 average rating, 118 reviews

Stellar Sellwood Carriage House

An inviting outdoor area features a wooden bench in a small courtyard, framed by a natural wood fence. The entrance to the studio is highlighted by large glass doors, allowing a view of warm interior lighting. Lush greenery adds a peaceful ambiance to the space.

4.94 out of 5 average rating, 783 reviews

Hawthorne Wisteria Retreat

The open living area features a spacious couch adorned with patterned cushions, a wooden coffee table, and a soft floor pouf. Bright natural light streams in through large windows, highlighting the airy loft concept and modern furnishings, including a view of a dining area in the background.

4.97 out of 5 average rating, 576 reviews

Modern Cozy Guest House in Hip NE Alberta/Williams

A modern studio casita features an open layout with high cathedral ceilings. A gray sectional sofa and armchair are arranged around a round coffee table on a soft area rug. The kitchen area offers sleek cabinetry and a breakfast bar with four stools. Natural light enters through large windows.