Guesthouse holiday rentals in Portland

Guesthouse in Westmoreland

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, 649 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.

4.98 out of 5 average rating, 221 reviews

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.

Guesthouse in Piedmont

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, 214 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 Arbor Lodge

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, 528 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

4.96 out of 5 average rating, 122 reviews

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.

Guesthouse in Multnomah

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

4.99 out of 5 average rating, 267 reviews

The entrance to the guesthouse features a warm wooden door framed by lush greenery. Potted plants and a natural wood stool create an inviting atmosphere. Soft string lights hang above, enhancing the serene outdoor space surrounded by trees.

Guesthouse in Woodlawn

Sorta Summer House w/ sauna & outdoor shower

The guesthouse is a private oasis in the city. It's surrounded by fruit trees and tall Chinese Mountain bamboo. It's a quick walk to Woodlawn Park, great coffee, a bakery, pizza, whiskey bar, a brewery, seasonal farmers market, and minutes from Alberta Arts District. The airy, open floor plan is filled with natural light, mixed textiles and warm woods. A cedar-surround outdoor shower and private 5x7 Finnish sauna lend to the spa-like setting. Guests say it’s hard to leave!

A charming guesthouse exterior is framed by lush greenery and colorful flowers. The house features large windows that allow natural light to fill the interior. The welcoming wooden doors add warmth, while a bicycle rests on the pathway, suggesting accessibility to nearby attractions.

5 out of 5 average rating, 261 reviews

Perfectly Portland Clinton St Guesthouse

This light & airy guesthouse is a private retreat in a perfect location, steps from Division St. Walkable to Salt & Straw & local eateries, food carts, and thrift shops. Prepare meals in the fully equipped kitchen or head out by foot to Oma’s Hideaway, a 2022 James Beard Award Finalists. Bring your bicycles to enjoy Clinton St Bike Boulevard or stroll to the Clinton St Theater. The guesthouse is family friendly, having special items to accommodate the littlest of guests.

4.97 out of 5 average rating, 426 reviews

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.

Guesthouse in Overlook

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 Foster-Powell

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, 379 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.

Guesthouse in Sullivan's Gulch

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.

5 out of 5 average rating, 433 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.

Guesthouse in Creston-Kenilworth

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, 137 reviews

The Kenilworth Guest House

Showcased in the Modern Home tour of Portland, this newly built ADU is the amazing creation of Portland architect Webster Wilson. A private, airy and elegant oasis set in urban Portland. A glass house with intentional frosted glass to ensure privacy. Escape and experience the elegant grace of this unique guesthouse. Threading the needle of a city lot, the Kenilworth House lives along side a 1905 Victorian, where the host resides.

4.96 out of 5 average rating, 250 reviews

The cottage exterior is showcased with a warm red facade and a welcoming entrance featuring a glass-paneled front door. A private patio with wooden doors opens to the yard, which is surrounded by fencing and landscaped with mulch and plants.

Guesthouse in Overlook

Private guesthouse w/ yard, firepit, patio, loft

We built this cottage in 2019 using many reclaimed materials, and we hope you love it as much as we do. Located just one block from all the best North Portland has to offer; coffee shops, brunch spots, neighborhood bars and shops. Very easy access to public transit (light rail and bus) and only one exit from downtown. 15 minutes to the airport and 8 minutes to Forest Park. Includes a spacious private yard/patio and firepit.

Popular amenities for Portland guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in South Tabor

An open living space features a comfortable sitting area with a sofa and stylish chairs. A dining table accommodates four, while the kitchen area showcases modern appliances. Natural light filters through multiple windows, illuminating the spacious sleeping area with a large bed in the background.

4.99 out of 5 average rating, 368 reviews

The Loft: Modern Open space in Southeast Portland

Guesthouse in Arbor Lodge

The exterior of the architect-designed cottage is shown, featuring a dark blue facade with white trim. Several large windows allow natural light to enter. A small pathway leads to the entrance, surrounded by minimal landscaping and a clear blue sky above.

4.96 out of 5 average rating, 456 reviews

Arbor Lodge Lodge- a relaxing oasis in the city

Guesthouse in Arbor Lodge

A modern living area is highlighted by a dark sofa adorned with patterned cushions. A green armchair complements the space, while natural light filters through three square windows. A large plant and woven wall decor add elements of nature and texture, creating a comfortable ambiance.

4.95 out of 5 average rating, 243 reviews

Artist loft in Arbor Lodge

Guesthouse in Forest Park

The exterior of a two-story guest house is depicted, featuring dark blue siding and a pitched roof. Surrounding evergreen trees provide a natural backdrop, while a gravel driveway leads to the home's garage. A wooden railing outlines an outdoor space adjacent to the house.

4.93 out of 5 average rating, 254 reviews

Forest views, hiking, family friendly!

4.95 out of 5 average rating, 238 reviews

An open living and dining area features a blend of warm tones on the walls. A wooden dining table is surrounded by white chairs, and large windows invite natural light. A comfortable sofa sits across from a small entertainment area with a TV and decorative elements.

Guesthouse in St. Johns

2-Bedroom Light & Bright St Johns Central House

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, 819 reviews

Modern Garden Studio Self Check & Private Entrance

4.95 out of 5 average rating, 183 reviews

The exterior of a newly constructed ADU features vibrant blue siding and a wooden overhang. A bright turquoise door provides a welcoming entry. Large windows allow natural light, while a small garden with low-maintenance plants enhances the landscape. A pathway leads to the entrance, framed by gravel.

Guesthouse in Concordia

The Little Blue ADU

The entrance to the converted garage features a vibrant red door framed by hanging flower pots. A small bicycle leans against the wooden fence, while potted plants line the entryway, creating an inviting approach to the lovely tiny home.

4.95 out of 5 average rating, 428 reviews

Hawthorne Crash Pad ~Your Own Private Retreat

Guesthouses with a patio

4.97 out of 5 average rating, 215 reviews

A bright and open living space showcases a kitchenette equipped with essential appliances, including a refrigerator and stove. A comfortable leather sofa is positioned on a plush area rug, while large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Guesthouse in Woodlawn

Woodlawn Cottage

4.96 out of 5 average rating, 222 reviews

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.

Guesthouse in Lents

Bright, Private & Cozy with Yard

4.99 out of 5 average rating, 127 reviews

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.

Guesthouse in Portland

Garden Home Getaway

Guesthouse in University Park

A private outdoor patio is surrounded by lush greenery and flowering plants. A simple dining table with two chairs sits on the stone-paved area, providing an inviting space for outdoor meals or coffee. Sunlight brightens the area, creating a serene atmosphere.

4.99 out of 5 average rating, 123 reviews

University of Portland private Guest House

5 out of 5 average rating, 101 reviews

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.

Guesthouse in Woodlawn

Private urban retreat, new build, 1bedroom, sleep4

4.99 out of 5 average rating, 104 reviews

The bathroom features a spacious walk-in shower with dual shower heads and a decorative blue herringbone tile accent wall. A modern sink vanity with dark wood cabinetry is accompanied by a wall-mounted rack displaying white towels. A large mirror is positioned above the sink, reflecting the light.

Guesthouse in Portland

Coda Guesthouse -New in 2024

4.96 out of 5 average rating, 194 reviews

An outdoor courtyard is illuminated by soft lighting, creating a serene evening ambiance. A picnic table and chairs are positioned under a wooden pergola, with a hammock suspended nearby. Lush greenery surrounds the space, enhancing the natural setting.

Guesthouse in Woodstock

Intimate Casita W/ Hot tub, Movie loft & Chiminea!

4.95 out of 5 average rating, 173 reviews

A modern bathroom features a countertop with a stylish basin sink and two circular mirrors above. Warm lighting is provided by pendant fixtures. A glass shower enclosure is visible, complemented by neutral tile flooring, while a plush rug provides comfort underfoot.

Guesthouse in Overlook

Luxury Spa Retreat Studio for 1-2 Guests

Guest house rentals with a washing machine and dryer

4.84 out of 5 average rating, 158 reviews

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.

Guesthouse in Eliot

The Haseman House

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, 517 reviews

Newly built studio in perfect SE location

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 out of 5 average rating, 364 reviews

Bright, modern, private home in lively SE Portland

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, 589 reviews

Little Cedar House High Speed WIFI - Super Clean

4.9 out of 5 average rating, 323 reviews

The exterior of a two-story cottage features a blend of yellow siding and rich wood accents. A vibrant blue door is framed by decorative planters with greenery. The backyard is enclosed, and outdoor seating is visible alongside a grill, enhancing the inviting outdoor space.

Guesthouse in Cully

Tucked Inn Cully

4.98 out of 5 average rating, 251 reviews

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.

Guesthouse in Hollywood

Centrally-located 1-bedroom escape in NE

Guesthouse in Rose City Park

The entrance to the guest house is framed by lush greenery and colorful flowers. A wooden door with a modern design is visible, complemented by a small seating area nearby. The path leading to the door is lined with stones, creating an inviting approach.

4.98 out of 5 average rating, 378 reviews

Peaceful + Modern : NE Portland

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.