Family-friendly holiday rentals in Clackamas River

Top of the World - Apartment near PDX w/ AC

This relaxing, private suite is perfect for your stay! Our organized space includes high-speed wifi, a gas fireplace, and even a washer and dryer. The kitchen is fully equipped with a dishwasher, fridge, Nespresso coffee maker, hot plate, cookware, and a three-in-one microwave/air fryer/mini baking oven. You have your own entrance and the space to yourself. Guests find the location very convenient and we often hear that the space feels comfortable, homey, and that we've "thought of everything!"

Kitchen · Indoor spaces · Value

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Kitchen · Indoor spaces · Getting around

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

Kitchen · Family · Breakfast

Bamboo & Lavender Luxury Container Retreat w/ View

Tucked inside a private bamboo grove and lavender field, Black Box Retreat is a brand-new luxury container home with sweeping valley views. Watch hummingbirds nest in the bamboo, deer graze at dusk, and sunsets turn golden from your private deck and fire pit. Inside, enjoy luxury finishes, room-darkening shades, a full kitchen, and dedicated workspace — perfect for couples, solo travelers, or groups of up to 3. World-class hiking, wineries, and the Oregon coast are just a short drive away.

Family · Kitchen · Solo travel

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.

Indoor spaces · 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.

Kitchen · Indoor spaces · Skiing

2.3k sqft Cozy Kid Friendly+ playground Toys Gym

The 2.3k sqft private space on the lower level of our home features a separate entrance and large windows with scenic views of greenery. Our family, including young children, lives upstairs, and we’ve added extra soundproofing for your comfort. You may occasionally hear faint footsteps or muted conversations during the day. The space is designed to be family-friendly, with fun activities for kids to enjoy. We appreciate your understanding and look forward to hosting you!

Kitchen · Family · Backyard

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 · Kitchen · Condition

Yeti's Tree House: Where Dreams Come True

“Best Tree House I’ve Ever Seen!” — Guest Climb into your childhood dream—a real treehouse held by four trees, 18 feet above the ground! Zip line through the woods, soak in the giant tub, and wander to the suspension bridge. It feels wonderfully wild and private, yet Portland’s famous attractions are just minutes away. A short 2-minute forest hike gets you there, so wear good shoes. Want your own guaranteed Bigfoot sighting? Contact Peter after booking :-)

Indoor spaces · Kitchen · Layout

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.

Family · Kitchen · Value

Willamette Riverfront Cottage near Portland

A private riverfront cottage on the Willamette in West Linn — 15 minutes to Portland, across from the great blue heron rookery. River views, resident wildlife, a fire pit, fast fiber Wi-Fi, and a fenced pet-friendly yard. A curated pillow bar, cafe-grade coffee bar, and a true work setup make it ideal for a slow reset or a longer stay. Rates vary by season; final pricing shows when you select dates.

Family · Kitchen · Pets

Farm Charm: 1000sq ft private studio in rural area

With unique vintage decor, this comfortable studio offers modern amenities in a peaceful country setting. The space has a private keypad entrance & 16 stairs (sorry, no elevator) to the guest studio attached to our home. Our friendly golden retriever Ollie will gladly greet you. Groceries & highway access are a mere 3 miles away. Portland is a short easy drive from our quiet country home.

Indoor spaces · Family · Accuracy