Guesthouse holiday rentals in Portland

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.

Location · Value · Comfort

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!

Family · Value · Amenities

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

Location · Value · Condition

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.

Value · Family · Laundry

Guesthouse in the Garden - Alberta Arts District

Enjoy a stay at this peaceful ~300 sq ft guest house located in the middle of the Alberta Arts District. Private entrance and entire place to yourself, no shared walls. Short stroll to great restaurants, art galleries, and shops. One block from Salt n Straw and several coffee shops. Great brunch, lunch, and dinner options all within walking distance. Reserved spot in our driveway for guests and plenty of free street parking available nearby as well.

Location · Value · TV

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.

Value · Family · Heating

Newly Built Guesthouse with Private Courtyard

Newly built one-bedroom guesthouse with charming private backyard in the popular Maplewood neighborhood. Light-filled, open floor plan with vaulted ceilings. Walk to Maplewood Coffee & Tea. Located 1 ½ miles from Multnomah Village, 3-4 miles from downtown Portland, Lewis & Clark College and OHSU, 7 miles from Nike. Easy day trips to the Oregon Coast, Columbia River Gorge, Mt Hood, and Yamhill County’s Wine Country. ASTR Permit #18-220704-HO

Location · Family · Long stay

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.

Value · Location · Outdoor spaces

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!

Value · Location · Parks

Canopy Loft PDX

The Canopy Loft is a sun filled, second story studio designed and built by my husband and I to be a cozy home away from home. The window views are full of foliage making you feel like you're up in the trees, hence the name. Our neighborhood is quiet and calm, and we are walking distance from downtown St Johns as well as many parks. The studio can also be turned into your own personal movie theater!

Location · Value · Access

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.

Location · Value · Backyard

Handcrafted Urban Hideaway | Private Driveway

Stay in this handcrafted rustic-industrial studio featuring reclaimed wood walls, 15-foot vaulted ceilings, and thoughtful custom details throughout. Private entrance and driveway, 10-minute walk to MAX light rail, and under 25 minutes to Mississippi Ave. Enjoy high-speed WiFi, a well-appointed kitchenette, and all the comforts of home in this unique urban Portland hideaway.

Family · Value · TV