Family-friendly vacation rentals in Damascus

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Top-rated family-friendly rentals in Damascus

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious covered patio features a rustic wood bar with barrel bases, accompanied by wooden seating and a table. Natural light filters in, illuminating the surrounding greenery. A barbecue grill stands ready for outdoor cooking, enhancing the inviting space for relaxation and gatherings.

Guest suite in Damascus

4.97 out of 5 average rating, 113 reviews

Unique Underground Speakeasy with hot tub

Escape the city in this unique underground stay. Located just outside the city and a quick drive to Mt. Hood. You are sure to leave relaxed and recharged after being surrounded by nature. Soak in your own private hot tub overlooking a forested ravine. The underground space is climate controlled equipped with AC/heat. Connect with nature while you enjoy the massive covered patio with a bbq and games. Ask the owners to hangout with the friendliest Pygmy goats and take photos to cherish the memory.

Guest favorite

The exterior of a two-story house is presented, featuring a gray roof and light siding. A well-maintained lawn with shrubs borders the driveway, leading to a garage with two doors. Towering evergreen trees provide a natural backdrop.

Guest suite in Gresham

4.88 out of 5 average rating, 121 reviews

Spacious two-room private suite. Clean and quiet!

Centrally located to Portland's cultural centers, brew pubs, wineries, and the unrivaled recreation of the Columbia River Gorge with world-class hiking, wind, and snow sports! 500 sq. ft. of comfort and cleanliness in two thoughtfully appointed rooms. Kitchenette with fridge, microwave, toaster, coffee-maker for breakfast prep. Bathroom with full laundry facilities. Two separate rooms and a private entrance. Come enjoy the solitude of our space or rest, fuel up, and launch to your adventures!

Top guest favorite

Guest suite in Gresham

4.96 out of 5 average rating, 165 reviews

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.

Superhost

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.

Guesthouse in Damascus

4.89 out of 5 average rating, 138 reviews

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.

Top guest favorite

A spacious living area features a large sectional sofa with patterned cushions, offering a comfortable place to relax. Natural light enters through sliding glass doors that lead to the outdoor space, while an adjacent dining area is visible, along with the kitchen in the background.

Guest suite in Happy Valley

5 out of 5 average rating, 116 reviews

Happy Valley - Serenity in the Suburbs

We offer you a spacious (1500 sq feet with 9 ft ceilings) daylight apartment which includes, 2 large bedrooms (one queen, two twins), full kitchen with basic supplies, full laundry, bathroom with shower, dining and living areas, office nook, covered outdoor patio for sitting, a secluded and quiet backyard great for birding, private parking spot and separate entry. Our property backs up to a protected nature area with a beautiful walking trail. Perfect for couples or a small family.

Top guest favorite

A cozy sleeping area features a comfortable queen bed with plush pillows and a soft white blanket. On either side, wooden nightstands hold stylish lamps that provide soft lighting. Above the bed, a floral artwork adds a subtle touch of color to the neutral wall.

Guest suite in Boring

4.96 out of 5 average rating, 499 reviews

Tiny Private Studio near Sandy, Oregon

Located between Mt. Hood and the Columbia Gorge! Cozy private studio, with a separate entrance on 2 quiet acres. This small studio has a comfortable queen bed with luxury linens throughout. A tiny kitchenette supplied with coffee, organic half and half, an assortment of tea, bottled water, and a few snacks. Wifi and YouTubeTV provided. Grocery stores, restaurants, movie theater, gym, and hiking trails just to name a few amenities all within 1 to 3 miles of our home.

Guest favorite

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

4.91 out of 5 average rating, 474 reviews

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!

Guest favorite

A cozy living area features a comfortable gray couch adorned with decorative pillows. A wooden coffee table sits in front, while two stools stand near a countertop. Sunlight streams through large windows, creating a bright and welcoming ambiance in the open kitchen space.

Guesthouse in Boring

4.91 out of 5 average rating, 188 reviews

Boring Bungalow /1 bedroom guesthouse with kitchen

Private and quaint one bedroom one bathroom guest house in beautiful Boring Oregon. Centrally located between beautiful Mt Hood recreation area, breathtaking Columbia River Gorge and the stunning Oregon Coast. You have a private entrance with keyless entry, a comfortable living area and well appointed kitchen. Free on site parking with room for boat and trailer if needed. All linens are provided, as well as a starter supply of toiletries, coffee and tea. STR784-22

Guest favorite

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

4.92 out of 5 average rating, 600 reviews

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.

Guest favorite

A grassy outdoor area features a wooden play structure with a slide and sand area, alongside a trampoline and a hammock. Two chairs in blue and white are positioned nearby, surrounded by lush trees and shrubs, creating a serene play space.

Home in Damascus

4.92 out of 5 average rating, 162 reviews

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.

Guest favorite

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

4.92 out of 5 average rating, 759 reviews

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.

Guest favorite

A cozy cabin interior features a wood stove providing warmth. A small kitchenette with a mini fridge is visible, alongside a dining table with two chairs. The wooden floor adds warmth, while a large window allows natural light to illuminate the space.

Guesthouse in Beavercreek

4.98 out of 5 average rating, 250 reviews

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.