Guesthouse holiday rentals in Portland

Guesthouse in North Portland

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, 281 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.

4.97 out of 5 average rating, 299 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.

Guesthouse in Clackamas

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Guesthouse in North Portland

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, 581 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

Guesthouse in Laurelhurst

A modern kitchen is showcased with sleek cabinetry and stainless steel appliances, including a refrigerator and an oven. A small dining table sits beside a cozy seating area, while a washer and dryer are positioned near the back. Natural wood ceilings add warmth to the space.

4.99 out of 5 average rating, 636 reviews

Little Cedar House Cottage near coffee and shops

5 year old 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 $30 fee per dog, per visit.

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.

5.0 out of 5 average rating, 127 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!

A detached studio features a charming A-frame design, surrounded by lush greenery. A stone patio with outdoor seating complements the inviting entrance, where large windows allow natural light to fill the space. The setting provides a serene atmosphere, ideal for relaxation.

4.98 out of 5 average rating, 698 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully 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.

A cozy seating area features two gray armchairs paired with a small round table and a decorative pouf. A wood accent wall complements the space, while a shelf displays books. Lighting from two lamps and a mounted TV adds warmth to the atmosphere.

4.97 out of 5 average rating, 414 reviews

Bridgetown Bungalow: The perfect cozy getaway!

Come retreat from the city in this gorgeous studio designed with a modern art deco flair and rustic cabin comfort. The cozy interior features a vaulted ceiling with original timber beams, craftsman trim, reclaimed wood accents, loft with a library ladder, a heated bathroom floor and walk-in shower. The full kitchen provides all the amenities you'll need for cooking & baking including basics like pots, pans, utensils, spices, oils, small appliances and several coffee-making options.

An architectural micro home is nestled among lush greenery, surrounded by trees. A wooden exterior enhances the natural setting. The structure features a small side porch and multiple large windows, allowing light to flood the interior. A pathway made of stones leads to the entrance.

4.85 out of 5 average rating, 192 reviews

The Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

The living area showcases a bright and airy design, featuring large windows that provide natural light. A plush blue sofa and a dark chair are positioned around a coffee table, while shelves filled with books add character. Art pieces adorn the walls, complemented by greenery.

4.99 out of 5 average rating, 657 reviews

Spacious Guesthouse with Creative Style and Local Charm

Our recently built, light filled and spacious ADU sits quietly in our back yard and above my painting studio. It's an open, airy and modern loft-style home with reclaimed fir floors, shelving, vanity, and doors. The queen size bed has a super comfy natural latex foam mattress and in the loft there is a fold out sofa with a full size memory foam sleeping pad. It has a well appointed kitchen and washer and dryer for your use. I provide coffee and tea for your stay as well.

A modern kitchen area features sleek white cabinetry and stainless steel appliances. A comfortably arranged living space includes a blue sofa and a small dining table with two stools. A hardwood floor complements the warm wooden ceiling, while a green plant adds a touch of freshness.

4.92 out of 5 average rating, 192 reviews

Private Guesthouse Above Detached Garage

Enjoy this modern, open, bright space! Sleep soundly in the queen bed, or on the sofa bed if you need the extra space. Full kitchen is ready for anything from prepping some of Portland's finest coffee to making dinner for your whole party (or maybe just heating up some of your leftovers from a delicious spot in the city!) Located less than a mile from Alberta St, Williams Ave, or Mississippi Ave - you'll always be close to the action! Enjoy NE Portland like a local!

Guesthouse in North Portland

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, 470 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.

Guesthouse in Southwest Portland

An open-concept space highlights bamboo flooring and large windows. A dining area features a wooden table with four chairs. The kitchen showcases modern appliances, with light fixtures illuminating the counter. A staircase leads to an upper level, accompanied by a decorative railing.

4.94 out of 5 average rating, 519 reviews

Secret Garden Guest House, Multnomah Village

2016 renovated backyard cottage located in "The Heart of Portland," the historic, now trendy Multnomah Village neighborhood next to The French Quarter! A quiet residential area in the Southwest quadrant of Portland. It's a quick walk to unique shops, coffee, and great restaurants. It's a 5-mile drive to downtown. It's complete w/ radiant floors, 2 bedrooms, full bathroom, full kitchen, dining & living room. Wireless Smart TV w/ Netflix.

Popular amenities for Portland guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Southwest Portland

4.99 out of 5 average rating, 103 reviews

Cottage

A spacious living area features a gray sofa accompanied by a wooden coffee table, set on a neutral rug. Large windows invite natural light, while a pair of doors opens to a green garden. Soft lighting is provided by a lamp beside the sofa.

4.98 out of 5 average rating, 711 reviews

Ivon Garden Cottage

An open living area is highlighted by large windows that invite ample natural light. The space features a comfortable couch adorned with yellow and gray cushions, a modern coffee table, and a cozy armchair. The kitchen is seamlessly integrated, showcasing sleek cabinetry and appliances.

4.98 out of 5 average rating, 183 reviews

The Kenilworth Guest House

The modern kitchen features navy blue cabinetry and a stainless steel refrigerator. A circular dining table complements the space, and light natural wood flooring enhances the inviting ambiance. Open shelving is adorned with decor and kitchen essentials, with natural light coming in from the window.

4.98 out of 5 average rating, 292 reviews

Centrally-located 1-bedroom escape in NE

A modern kitchen is highlighted by large skylights and sleek wooden accents. Stainless steel appliances complement white cabinetry and a spacious countertop. A dining table with green chairs is positioned in front of a vibrant view through large windows, enhancing natural light throughout the space.

4.97 out of 5 average rating, 110 reviews

Luxury Cabin in the City

4.97 out of 5 average rating, 184 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.

Guesthouse in West Linn

Charming one bedroom apartment in the forest.

The charming entrance features a wooden door with glass panels, framed by large windows on each side. Decorative planters with colorful flowers sit on either side of the subdued walkway, which is bordered by a stone path leading to the door.

4.97 out of 5 average rating, 586 reviews

ROSE CITY PARK Guesthouse!

A modern kitchen is displayed, featuring white cabinetry and stainless steel appliances. A wooden dining table is set in the center, surrounded by bright yellow chairs. The countertop is equipped with essential cooking tools, complemented by soft under-cabinet lighting.

5.0 out of 5 average rating, 364 reviews

Our Guesthouse - Alberta Park - 2 bedrooms (queen)

Guesthouses with a patio

The living area features a high vaulted ceiling with wooden beams, a spacious seating arrangement including a navy blue couch and a round plush armchair. A cozy loft is visible above, and a kitchenette with modern appliances is situated in the background. Decorative plants add a touch of greenery.

4.98 out of 5 average rating, 101 reviews

Fir Grove Tree House

4.99 out of 5 average rating, 165 reviews

Guesthouse in Vancouver

Fern Cottage

4.92 out of 5 average rating, 132 reviews

City Cottage with Country Feel

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, 145 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.

5.0 out of 5 average rating, 123 reviews

Private urban retreat, new build, 1bedroom, sleep4

A bright bedroom features a spacious bed with crisp white linens, complemented by a subtle fan overhead. A wall-mounted TV is positioned across from the bed. Natural light enters through the window, where curtain panels add a touch of warmth to the space.

4.99 out of 5 average rating, 112 reviews

Bright & Peaceful Retreat in the heart of NE PDX

4.96 out of 5 average rating, 105 reviews

Wellness Oasis w/ Sauna, Hot Tub & Fireplace

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.

4.97 out of 5 average rating, 178 reviews

The Loft in Hawthorne Tabor

Guest house rentals with a washing machine and dryer

Guesthouse in Northwest Portland

An open bedroom features a spacious bed with a light blue quilt and matching accent pillows. A textured wall art piece is displayed above the headboard. Natural light illuminates the neutral-toned carpet, complemented by a small wooden nightstand and a mirror reflecting the inviting space.

4.93 out of 5 average rating, 223 reviews

Queen Anne Guest Apt. In Historic District

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, 423 reviews

Award-Winning Guest House with 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, 577 reviews

Newly built studio in perfect SE location

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.

4.83 out of 5 average rating, 207 reviews

Private Oasis! Cozy & Close to Everything!

A modern kitchen area showcases sleek cabinetry and stainless steel appliances. An inviting kitchen island with seating is complemented by wooden chairs. Natural light filters through a skylight and French doors, enhancing the space's openness. The dark accent wall contrasts with light countertops.

4.96 out of 5 average rating, 561 reviews

Fresh North Portland Studio

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.

5.0 out of 5 average rating, 423 reviews

Bright, modern, private home in lively SE Portland

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, 810 reviews

Hawthorne Wisteria Retreat

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.