Family-friendly holiday rentals in Damascus

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.

Indoor spaces · Family · Accuracy

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

Family · Kitchen · Parking

The Story House

Between the lights of Portland and the slopes of Mt. Hood stands a whimsical woods of giant firs, feathery cedars and old mossy maples. Midst a maze of paths and ferns is a cozy cabin full of delightful art. Browse the uncommon birdhouses and their stories. Just steps outside the French doors is a lighted path to the bathhouse (the only bathroom) with toilet, shower, clawfoot tub and washer/dryer. Walk the paths, soak in the hot tub and end your day in the peace and quiet of a private cabin.

Family · Indoor spaces · Comfort

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

Family · Indoor spaces · Getting around

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.

Family · Kitchen · Hospitality

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. We have friendly dogs you may see outside, and we do not allow pets. No smoking in the unit. There is a smoking hut on the property you are free to use should you choose to (bring a container with you to dispose the remnants). SE Portland is a 30 min drive and downtown Portland a 45 min drive. One hour to Mt. Hood, & falls in the Gorge. Pool open 6/15 through 9/5.

Family · Kitchen · Cleanliness

Columbia Gorge Retreat with a view

Whole private three bedroom home, 1400 square feet on two acres with view of the Columbia River and a cozy feel. Located within the Columbia River Gorge National Scenic Area with close access to hiking, Multnomah Falls Lodge, Vista House, Historic Troutdale, and 40 minutes to Hood River. 20 Minutes to Portland Airport. Includes laundry, wifi, towels, coffee, tea, condiments and other essentials. See more photos of the area and share your own on Instagram #columbiagorgeretreat

Indoor spaces · Family · Nearby

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.

Indoor spaces · Family · Shared spaces

Modern Spacious Private Guesthouse!

This spacious guesthouse is the perfect spot to relax and unwind, located conveniently just a few minutes from an abundance of restaurants and stores. The home is equipped with a queen bed and futon, kitchenette, and dining area. For your convenience, you have your own washer and dryer in the unit. Explore stunning Oregon beauty by adventuring to the nearby parks and trails. If you'd rather cozy up inside, the guesthouse has free-wifi and Netflix.

Kitchen · Family · Long stay

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like glamping, then look no further! The fire pit, creative décor, A/C mini split, table/chairs, the 'bathroom' is a weekly serviced clean and private portapotty (equals most of cleaning fee), cold water sink, outdoor covered heated shower, TV, and WIFI. We welcome ALL colors, religions, LGBTQ , Cannabis and Cigs OK by fire pit and coffee bar areas only.

Kitchen · Family · Check-in

Breathtaking views, Fish, Ski, Mt. Bike, or Hike

Experience a charming two-bedroom suite in the daylight basement of a two-story home, complete with a private entrance and covered patio. Enjoy breathtaking views of Mt. Hood and the Sandy River from your beautiful backyard. Nestled near Oxbow Park, you're just minutes from shops, restaurants, and outdoor adventures in the Columbia River Gorge and beyond. With the Portland airport only 25 minutes away, this cozy retreat is the perfect getaway!

Family · Kitchen · Barbecue

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.

Family · Kitchen · Cleanliness