Guest house holiday rentals in Portland

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.

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

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.

Chic Guest House in the Heart of the City

This guest house boasts designer fixtures and finishes created to exude equal levels of style and comfort. White walls, herringbone wood floors, and tall vaulted ceilings create a natural and airy ambiance that flows throughout every room. 1-level, ADA-friendly, with walk-in curbless shower and plenty of space to maneuver in spa-like bathroom and throughout. Our guests have full access to the private freestanding guest house, as well as the concrete patio just outside the unit.

Private Studio in NE Portland

Escape to a charming guesthouse in Portland’s Alberta Arts District, brimming with eateries, murals, coffee shops, bars, galleries and unique shops. Relax in your private retreat, furnished with a queen bed, fold-out couch, fully-equipped kitchen, and serene outdoor space. The space is nestled in the backyard, separate from the main house, ensuring ultimate privacy & tranquility. Relax and unwind with everything you'll need for your time in Portland.

Romantic Casita. HotTub and Firepit. Pets Welcome!

Come and stay in our romantic, Mediterranean Casita. This private cabin is built for singles and couples. Featuring a hot tub, fenced courtyard, fire pit, covered patio, white Linens, handmade ceramics, rustic furniture, peaceful art and off street parking. Though secluded, you're just a short walk from the vibrant Woodstock BLVD. Enjoy a unique, tranquil retreat designed for relaxation and intimacy, comfortably fitting two guests. Pet's are welcome.

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.

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.

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!

Explore Portland on Foot from Your Modern Retreat

Welcome to The LoftHaus. Stroll through a luscious landscaped garden and past a bubbling fountain to reach this light-filled, creative living space. A roll-up glass garage door in the bedroom offers a connection with the outside world while flooding the room with natural light. Accepting guests and implementing extra cleaning protocols. Excellent wireless internet speeds!

Cozy Clinton Cottage (close-in SE off Division)

Our lovingly renovated, light-filled guest cottage is detached from the main house, with a private entrance and outdoor seating area. Our central location is great for exploring all of the best that Portland has to offer, with easy access to public transit and bike routes. The space is very cozy and has everything you need for a fantastic Portland vacation or work trip.

Private Arbor Lodge Cottage

Architect designed Arbor Lodge cottage. Located in a quiet neighborhood 1/2 block from Arbor Lodge Park. The space is bright and gets a lot of natural light. I hope you find it comfortable and relaxing. It is also conveniently located to many nearby shops, grocery store, restaurants, pubs and transit connections (light rail and bus).