House holiday rentals in Raleigh Hills

The Cheese on Cheshire

Centrally located, freshly remodeled 3 beds, 1.5 baths with a yard and fire pit. We hope you don't mind it being a bit cheesy... We had a ton of fun coming with this theme. The property is on Cheshire, with a little research we learned that Cheshire is an area in England and they make some cheese there hence The Cheese on Cheshire. The building is a duplex so there's a chance you could book both sides for large group. Right in the heart of Beaverton you'll love the convenience of this location.

Your newly remodeled home away from home

Conveniently located near Hwy 217, Hwy 99W, I-5, and Hwy 26. Parking: attached private garage plus driveway. The unit is located on the 2nd floor of a 4-Plex. 60" 4K Samsung in the living room 42" LG and 40 " Sony in bedrooms Netflix, Prime Video and fuboTV WiFi download speed up to 400 Mbps; upload speed up to 10 Mbps Washer/dryer on premises Smoking or vaping is strictly prohibited in property. Please consider booking some other Airbnb property if anyone of your party is a smoker/vaper.

Portland Southwest Suite Stay

Cozy, top 1% rated SW Portland retreat with privacy, comfort and exceptional hospitality. You’ll love the spotless, comfortable space, quiet and safe neighborhood, and incredibly comfy bed. Seamless 24-hr self check-in, continental breakfast, thoughtful family-friendly amenities (crib, change table, high chair, sofa bed). With a private entrance, covered outdoor seating, easy transit access, parks, dining, OHSU, Oregon Zoo, Japanese Gardens and downtown. Best for 1-2 adults + small children.

Cozy modern staycation workplace close to downtown

Entire space is very private. Enjoy the cozy modern 1 bedroom queen bed, 2 large sofas that are comfortable to sleep on, oversize soaking tub large walk-in closet , 2 TVs, Blue Ray player, stereo, gorgeous private garden with table seating & tranquil water feature, & private entry. 5 minute drive to downtown, 2 minute walk to Forest Park & Marquam trails. Several amazing restaurants just minutes away. There is a pet fee of $40 each pet. Preferably just one pet or the fee is $70 for two.

Hidden Garden Cottage

This 850 sf. cottage is a century old but was completely updated 12 years ago with era-appropriate furnishings, giving it a period (and safe) feel. Breakfast goodies, art, books, and a woodstove make it cozy. It sits on half an acre so lots of room for kids . It's in SW Portland, minutes from downtown. It's quiet, great for working or vacationing. An outdoor fire pit and gardens make it unique. There's even a zip line for kids. Family gatherings also fine. (Note: There is a $60 fee per dog.)

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Spacious and serene. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Please note that owners live on site as required by Portland laws. Located in a quiet neighborhood, close to hiking trails. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland

Peaceful Garden House in SW Portland

This darling 1940's home sits on 1/4 acre and is nestled in a peaceful neighborhood in Southwest Portland. It gets tons of natural light, has greenery from every window, is super private and full of vintage charm and character. The home has served as a source of inspiration for the artists, writers and herbalists who’ve lived here throughout the years and now you can experience it for yourself! If you’re looking for an oasis of calm just outside of Portland, you've found the perfect spot.

Rock N Roll House + Hot Tub

Featured in The Destination Channel’s TV show “Staycation- Sports Edition” in the fall of 2025 and found on YouTube. Contemporary-style music-themed home. Jam out with instruments, classic albums and record player by the pool table. Stunning gourmet kitchen. Big lawn and deck with teak dining table and bbq. Hot tub plus gas and real fire pits. Garage is packed! Ping pong table, pinball, foosball, Pop-a-Shot basketball, Treadmill, Peloton bike, dumbbells, and four mountain bikes+helmets.

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

#StayInMyDistrict Raleigh Hills Serene Havens Nest

Stay in My District Raleigh Hills! Convenient to Shopping, Dining & Entertainment. Single level guest home is spacious, bright and tastefully appointed. Nestled down a private driveway on a quiet culdesac, w/ all the conveniences of the City. Close to SW Beaverton Hillsdale Hghwy & US 26, 15 min downtown PDX. This NEW private guest house is a cozy 500 ft.², with Queen bed/ sofa bed /1 bath. Sleeps up to 4. Full Kitchen, Washer/Dryer, FREE Parking, Smart TV & WIFI.

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.