Guest house holiday rentals in Portland

Pet Friendly, Cozy & Curated Designer Guesthouse

Our guesthouse is situated behind our home, located on a large corner lot in beautiful Grant Park. Surrounded by picturesque homes and tree-canopied streets, it’s a perfect combination of peace and quiet alongside accessibility. Dozens of local shops and fabulous PDX restaurants, just a 10 minute walk away. Five minutes to freeway access, guests enjoy convenient options, exclusive privacy, and detailed designer touches. A perfect base camp for an extended PNW exploration, or a weekend getaway!

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.

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!!

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

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 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 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.

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.

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.

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.

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.