Guesthouse holiday rentals in Portland

4.97 out of 5 average rating, 182 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.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

5.0 out of 5 average rating, 281 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, 276 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 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, 203 reviews

Private Oasis! Cozy & Close to Everything!

Beautiful, one of a kind guest house nestled in one of Portland's most desirable locations! This chic and cozy space features vaulted ceilings, all new appliances, comfortable furniture, and tons of natural light! A quiet street, peaceful atmosphere (and awesome soaking tub) make this the perfect spot for relaxation. Enjoy exploring the surrounding neighborhood and easily walk to shops, restaurants, bars and Laurelhurst Park! Central location allows quick travel to other areas of the city!

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, 574 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.

5.0 out of 5 average rating, 120 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!

The exterior of a charming blue guest house is framed by greenery and decorative stones. A welcoming entryway is highlighted with two white chairs, while a wooden awning provides shade over the entrance. The path to the door is lined with pavers and gravel.

4.99 out of 5 average rating, 223 reviews

Willow Tree Guesthouse

Pet friendly guest house in SE Portland 1 block from the heart of SE Division street. Located on a quiet dead-end street, with a full kitchen, ground floor bedroom/bathroom, spacious walk-in shower, and super cozy upstairs loft makes for the perfect work remote office. Grocery stores in every direction, neighborhood wine shop, and weed shop, restaurants and bars right around the corner. Location and walk score - 100! Gigabit fiber internet - good bandwidth for the digital nomads!

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, 689 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.

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, 463 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.

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, 418 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 Northwest Portland

The guest house is set against a lush backdrop of greenery, featuring large windows that provide views of the surrounding nature. A pool is positioned in front, accompanied by two wooden lounge chairs and a shaded umbrella, creating a serene outdoor relaxation area.

4.92 out of 5 average rating, 108 reviews

Poolhouse of Portland Architectural Gem

Private guest house adjacent to Pietro Belluschi's "Sutor House", featured in Dec 2017 Dwell Magazine. Pool-house is 750 square feet, and features a master bedroom, full bath, living area with kitchenette, and access to and shared use (With our family) of the swimming pool in summer months (June, July, August). Surrounded by private wooded garden with Japanese plantings and water features. Located in Portland's West Hills, just minutes from Downtown.

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, 514 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.

Popular amenities for Portland guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Beavercreek

A cozy cabin interior features a wood stove providing warmth. A small kitchenette with a mini fridge is visible, alongside a dining table with two chairs. The wooden floor adds warmth, while a large window allows natural light to illuminate the space.

4.97 out of 5 average rating, 356 reviews

Muse Cabin in old growth forest w/cedar hot tub

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, 707 reviews

Ivon Garden Cottage

The entrance to the guesthouse features double black doors with glass panes, set against a modern grey exterior. Lush greenery and potted plants frame the doorway, enhancing the welcoming atmosphere. The open doorway reveals a glimpse of a cozy interior with warm wooden flooring.

4.98 out of 5 average rating, 263 reviews

Waterfall Lodge

Guesthouse in Laurelhurst

A well-lit guest space includes a spacious bed, modern television, and a chic coffee table. Two large windows offer ample natural light, accompanied by a small dining set and a comfortable chair. The hardwood floor adds warmth to the inviting atmosphere.

4.93 out of 5 average rating, 107 reviews

Stylish Laurelhurst Guesthouse

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.

4.98 out of 5 average rating, 102 reviews

Luxury Cabin in the City

A modern studio space showcases a spacious bed with soft bedding, flanked by a decorative wall featuring floral designs. A cozy seating area is present alongside a dining nook, creating a functional layout. Natural light filters through the nearby window, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 194 reviews

Three Wishes Studio

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, 565 reviews

Newly built studio in perfect SE location

The exterior of the bungalow features a green facade with double glass doors providing entrance. A landscaped area includes a small tree and planters, with patio seating nearby. The surrounding greenery presents a welcoming atmosphere.

4.97 out of 5 average rating, 1294 reviews

Creative & Clean Bungalow in Portland Hot Spot

Guesthouses with a patio

The entrance is framed by a wooden awning, showcasing double glass doors. A comfortable chair is positioned to the side, accompanied by decorative pillows. Potted plants adorn the entryway, enhancing the inviting atmosphere of the cottage.

4.92 out of 5 average rating, 123 reviews

City Cottage with Country Feel

4.96 out of 5 average rating, 265 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. Hot-tub, Movie Loft and Chiminea.

A charming exterior of the guesthouse is surrounded by lush greenery and various plants. The driveway leads up to the house, framed by a rustic wooden fence. Sunlight shines on the inviting entrance, showcasing a blend of natural elements and a tranquil atmosphere.

4.93 out of 5 average rating, 148 reviews

Cozy Loft With Hot Tub

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, 121 reviews

Private urban retreat, new build, 1bedroom, sleep4

4.98 out of 5 average rating, 133 reviews

Coda | Walkable Woodstock Guesthouse | Portland

4.94 out of 5 average rating, 188 reviews

The Yellow Cottage - Private, Peaceful, & Near PDX

A spacious studio is highlighted by exposed wooden beams overhead. A large bed with neutral bedding occupies one side, while a kitchenette and open shelving are visible on the opposite side. Natural light flows through sliding glass doors, enhancing the airy atmosphere.

5.0 out of 5 average rating, 313 reviews

Finch Studio Cottage in Montavilla, Italy

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, 175 reviews

The Kenilworth Guest House

Guest house rentals with a washing machine and dryer

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, 553 reviews

Fresh North Portland Studio

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.

4.95 out of 5 average rating, 504 reviews

Private Arbor Lodge Cottage

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, 416 reviews

Bright, modern, private home in lively SE Portland

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, 173 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, 460 reviews

Maple Cottage PDX/ Fun Historic Mississippi Ave.

The exterior of the cottage features a charming design accented by decorative string lights overhead. A small stone path leads to a cozy patio with seating for two, surrounded by greenery and soft outdoor lighting, creating an inviting setting as evening approaches.

5.0 out of 5 average rating, 139 reviews

Overlook Cottage, Upscale w/ Off-Street Parking!

Guesthouse in Laurelhurst

The living area features large windows allowing natural light to fill the space. A comfortable sofa is complemented by a round coffee table and a stylish accent chair. A colorful area rug adds warmth, while modern artwork enhances the contemporary decor.

4.95 out of 5 average rating, 437 reviews

Chic Guest House in the Heart of the City

The spacious interior features tall ceilings and an open layout. A comfortable seating area with a blue couch sits near a bright window. The well-equipped kitchen and dining space are visible, alongside a sleeping area with neatly rolled towels on the bed.