Family-friendly holiday rentals in Damascus

4.96 out of 5 average rating, 180 reviews

The exterior of a two-story house is presented, featuring a red and gray façade with white trim. A welcoming porch with decorative railings extends along the front, surrounded by lush greenery. A chimney rises from the roof, complementing the home's charming architectural details.

Guest suite in Gresham

Sweet Private Suite in Historic Home

Mary and I love hosting people who appreciate a comfortable experience and beautiful space. Our Private Suite is located in an idyllic setting central to all the activities, great food and nature that the greater Portland area is known for, but without the "junk" that comes with being in the city. Short drives to Portland, Mt Hood hiking and skiing, the Columbia River, Multnomah Falls and great entertainment at McMenamin's "Edgefield (15 Min)" and "Grand Lodge" (35 min.). Infants 0-2 welcome.

4.89 out of 5 average rating, 152 reviews

A serene bedroom features a spacious bed adorned with an assortment of decorative pillows. Two modern bedside lamps flank the bed, providing soft light. A piece of abstract artwork hangs above the headboard, complemented by greenery on the side, creating a relaxing atmosphere.

Guest house in Damascus

Hygge House-luxurious secluded 3BR guesthouse

The Hygge House PNW is a place to unwind, get cozy and enjoy the company of those you love. Cuddle up with a cup of tea or a good book and enjoy a restful retreat. Enjoy country vibes while being moments away from Happy Valley City Center. Whether you're in town visiting friends and family or looking to experience everything Portland has to offer, the Hygge House has you covered. We hope you enjoy your time spent here and leave feeling relaxed and more connected with the ones you love.

4.91 out of 5 average rating, 500 reviews

A charming storybook cabin is framed by lush trees, adorned with hanging lights that warm the inviting facade. Flower boxes beneath the windows add color, while a pink door and decorative accents enhance the whimsical aesthetic. An ornamental fence encloses a neat garden area.

Farm stay in Oregon City

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

4.92 out of 5 average rating, 624 reviews

A serene garden scene features a waterfall cascading over natural stone, surrounded by lush greenery and colorful flowers. A small pond is visible at the base of the waterfall, complemented by a tranquil statue. Various plants add vibrant textures and colors throughout the landscape.

Guest suite in Damascus

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

4.86 out of 5 average rating, 200 reviews

The living area features knotty pine walls and ceiling, with large windows offering views of lush greenery. A blue couch is positioned across from a compact table suitable for dining or work. A patterned area rug adds texture, complementing the overall cozy atmosphere.

Tiny home in Gresham

Tiny Cabin Guesthouse

Take the flagstone path to this cozy, modern cabin (tiny home) with knotty pine walls, warm light, and a bedroom/loft that overlooks a wildly landscaped yard and garden. This 300 sq ft guest house features everything you need for a comfortable stay in the great PNW. Please note: Before booking, be aware the toilet in this home is a composting toilet, not flushing. It will be clean and ready to use with instructions available in the home.

4.93 out of 5 average rating, 175 reviews

A cozy living area features a sectional couch adorned with decorative pillows. A wooden dining table with sturdy chairs is positioned nearby. Art prints are displayed on the walls above the couch, and a floor lamp adds soft illumination to the space.

Home in Damascus

Foxglove Farm Private Guest Suite

Enjoy a stay in a ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

4.92 out of 5 average rating, 781 reviews

The entrance to the tiny house features a vibrant green door framed by natural wood, leading to a small porch area. A chair sits to the side, with lush greenery surrounding the property, enhancing the connection with nature.

Tiny home in Damascus

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

4.86 out of 5 average rating, 874 reviews

The exterior of a bright-red double decker bus is showcased, nestled in a shaded outdoor area. Adirondack chairs are positioned nearby, and cafe lights are strung above, creating an inviting space to relax. The bus's large windows allow natural light to filter in.

Place to stay in Russell

The Royal Scott Double Decker Bus

Our tiny home started life as a commuter bus in Manchester, England, in 1953, then did stints in San Francisco and Mt. St. Helens before finding a home as the Grilled Cheese Grill in Portland. Now it’s been reimagined as a mid century modern-inspired tiny home, with whimsical painting details from one of its former lives and fresh new handmade details that make it a cozy, inspiring stay. Find more on IG @smore.life

4.88 out of 5 average rating, 110 reviews

A modern kitchen is arranged with sleek cabinets and stainless steel appliances, featuring an island with a round dining table. Four black chairs complement the wood flooring, while a plant adds a touch of greenery in the corner. Light enters through a window, enhancing the bright atmosphere.

Flat in Damascus

Modern Townhouse

Newly built gated Modern Townhouse. Beautiful and scenic drive to Timberline Lodge / Mt. Hood Ski Bowl. 25 minute drive to downtown Portland. 15 minute drive to Clackamas Town Center. Minutes away from 172nd / Sunnyside shopping center and restsurants. Close drive to Multnomah Falls. Close drive to Vista House view point. Lots of hikes and trails nearby.

4.76 out of 5 average rating, 157 reviews

A cozy seating area is presented with a full-size daybed/couch, accompanied by a framed mirror and a wall-mounted television. A rug with geometric patterns enhances the space, while a lamp provides soft illumination. An accent pillow showcases a welcoming phrase.

Apartment in Troutdale

Modern Studio Apartment Near Edgefield!

Fantastic location close to Edgefield & downtown, historic Troutdale. Features a full size daybed/couch and a small kitchen with a modern look. Comfortable, uniquely designed space. Features 1 BD/LVG RM, 1BA Studio with private entrance. Relax in this calm, stylish space after enjoying a concert at The Edgefield or a day exploring the Gorge!

4.95 out of 5 average rating, 156 reviews

A vibrant tiny home with a red exterior and blue trim is framed by a cluster of blooming pink flowers in the foreground. The welcoming entrance is highlighted by warm lighting, complementing the colorful garden that surrounds the property.

Tiny home in McLoughlin

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.

Guest house in Oregon City

A charming red cottage is nestled among lush greenery, with large windows framed in gray. A moss-covered tree stands nearby, adding to the serene woodland setting. Soft light emanates from the cottage's windows, suggesting a cozy atmosphere inside.

5 out of 5 average rating, 602 reviews

Cottage in the Country

At the end of a long driveway through large evergreen trees sits this 600 sq ft cottage studio at the edge of the woods, ready to provide you with a relaxing country retreat. Enjoy this lovely remodeled guest house with a woodland landscape outside your doors.

Popular amenities for Damascus family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 433 reviews

A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.

Guest suite in Milwaukie

River Forest Lake Apt w/hot tub. HOT find!

4.92 out of 5 average rating, 197 reviews

A warm bedroom features a spacious bed dressed in white linens and a navy throw blanket. Wooden accents and built-in lighting create a cozy ambiance. A decorative rug is placed under a wooden bench, and a chair sits nearby. A window allows natural light to enter.

Flat in Montavilla

Hip & Spacious: Mt. Tabor Haven with Hot Tub!

4.84 out of 5 average rating, 131 reviews

A vibrant pool area is highlighted with colorful lights and surrounded by lush greenery. Lounge chairs are positioned for relaxation, and an umbrella offers shade. String lights create a warm ambiance over the space, enhancing the inviting atmosphere.

Guest house in Portland

Cascadia Cabana | Poolside Suite with Spa

4.94 out of 5 average rating, 254 reviews

A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.

Home in Portland

Spacious Forest Retreat w/ Hot Tub & Views

4.88 out of 5 average rating, 251 reviews

A bedroom features a queen bed with a decorative metal frame, dressed in light bedding with green accents. Two bedside lamps provide gentle illumination, and French doors open to a balcony, offering views of the surrounding greenery. Soft carpeting adds warmth to the space.

Flat in Milwaukie

Indulge in Rare Riverside Retreat

4.93 out of 5 average rating, 538 reviews

Two elegant cocktail glasses filled with ice are displayed on a wooden railing. In the background, a panoramic view of a lush green landscape and rolling hills can be seen, with the prominent snow-capped peak of Mt. Hood against a clear blue sky.

Flat in Oregon City

Sunday Quiet, awesome Hood view, hot tub!

Tiny home in Foster-Powell

4.87 out of 5 average rating, 488 reviews

Margaux | Airstream Glamping in the Heart of PDX

4.87 out of 5 average rating, 103 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Lents

RoofTop FirePit, HotTub & Outdoor Theater

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 724 reviews

The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.

Cabin in Milwaukie

Rustic Creekside Cabin

4.93 out of 5 average rating, 148 reviews

The living room features a playful foosball table in the foreground, with a cozy seating arrangement including a green sofa and an accent chair. A large window allows natural light to fill the space, complemented by soft drapes and a decorative wall mural depicting mountains.

Home in Gresham

PNW Sanctuary at the Gorge Family friendly Ranch

4.92 out of 5 average rating, 145 reviews

The open living space features a sectional couch with cushions, a wooden dining table, and chairs in a well-lit area. A television is mounted on the wall, with kitchen and dining areas visible in the background, illuminated by natural light from large windows.

Home in Gladstone

Forested Hygge House Getaway

4.97 out of 5 average rating, 966 reviews

The bathroom features a jetted tub surrounded by elegant tiles and candles. A large mirror enhances the space, while neatly arranged towels and plush robes are visible. Soft lighting and natural light from the window create a serene environment, emphasizing the calm aesthetic.

Guest suite in Troutdale

Amazing VIEW & Private Entry/Jetted Tub near Falls

4.96 out of 5 average rating, 222 reviews

A cozy studio space is depicted, showcasing a comfortable seating area with a neutral-toned sofa. An open kitchen with bar seating is visible in the background, alongside large glass doors leading to a fenced backyard. A television stands against the wall, ready for entertainment.

Guest house in Lents

Bright, Private & Cozy with Yard

4.92 out of 5 average rating, 180 reviews

A charming blue cottage is framed by a welcoming front porch with wooden railings. Lush green plants and purple flowers decorate the landscape. An American flag is displayed on the railing, and a car is parked in the driveway alongside the property.

Bungalow in Gladstone

The Wee Humble Cottage

4.81 out of 5 average rating, 101 reviews

A compact kitchenette features dark cabinets and a sink, complemented by a small seating area visible through an open door to a fenced yard. A pullout couch with cushions and a nearby wall-mounted table are also included in the cozy space.

Guest suite in Troutdale

Fresh + Clean, Walk to Edgefield and Town

4.88 out of 5 average rating, 169 reviews

A bright living area features a red sectional sofa adorned with decorative throw pillows. Two pieces of abstract wall art add color, while a wooden side table sits beside the sofa. Light enters through a window, enhancing the space's warmth.

Holiday home in Portland

Lovely 1-bed vacation home w/ off street parking.

Family-friendly home rentals with a pool

Guest suite in Rose City Park

The kitchenette features sleek white cabinetry, a stainless steel refrigerator, and modern appliances. A round black table with two colorful chairs is situated on a patterned rug, complemented by open shelving displaying cups and utensils. The space is illuminated by natural light from a nearby doorway.

4.95 out of 5 average rating, 464 reviews

Rose City Retreat

4.96 out of 5 average rating, 108 reviews

A bright yellow door welcomes guests, set against exposed brick and green wall textures. Stone steps lead up towards the entrance, framed by potted plants. The inviting doormat displays the word 'WELCOME', enhancing the cheerful entrance to the apartment.

Guest suite in Eliot

Garden Apartment in the Heart of Portland

4.96 out of 5 average rating, 110 reviews

A secluded hot tub is nestled among the trees, surrounded by vibrant green moss and natural elements. Two wooden stools are positioned nearby, while a rustic wooden pathway leads through the forest. The serene atmosphere is enhanced by the gentle sound of the nearby creek.

Cabin in Rhododendron

2BR Dog friendly Mount Hood cabin with hot tub!

4.93 out of 5 average rating, 102 reviews

Home in Rhododendron

Hot Tub + Forest Views | Mt Hood Getaway

4.95 out of 5 average rating, 295 reviews

The living room features a comfortable leather sectional sofa and two armchairs, paired with a coffee table. Natural light filters through the window blinds, illuminating the patterned area rug on the carpeted floor. A large television is positioned on a wooden stand.

Guest suite in Welches

Mt. Hood Autumn Getaway: 1BR Apartment

5 out of 5 average rating, 474 reviews

A golfer stands on a green tee-off area, facing a serene landscape filled with tall trees and lush grass. A small bucket of ice is positioned nearby, amidst the tranquil surroundings of a picturesque outdoor space.

Guest house in Newberg

Wine Country Spa House - Hot Tub/Sauna/Pool

4.98 out of 5 average rating, 214 reviews

A charming treehouse is suspended between large fir trees, featuring a wooden deck with multiple seating areas. Large windows provide natural light, and the surrounding forest greenery adds to the tranquil setting. The pathway beneath is lined with gravel, leading to the entrance.

Treehouse in Mt Hood

Beautiful, Magical, Treehouse