Family-friendly vacation rentals in Clackamas County

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Top-rated family-friendly rentals in Clackamas County

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Guest favorite

Guest suite in Estacada

4.75 out of 5 average rating, 445 reviews

Country Living in a Forest Setting

Come stay in your own cozy, rustic mini apartment, a little over 25 minutes from the Portland suburbs, and about 45 minutes from downtown Portland. Our home sits on two wooded acres. You'll have a private deck, private bathroom, private entrance, and private living space. There is a queen bed in the bedroom and a futon/sofa in the living area that makes a twin-size bed. Check-in time is after 4 pm. Early check-in is possible, just contact us. No Smokers! One pet on approval, up to 45lbs.

Top guest favorite

Apartment in Sandy

4.99 out of 5 average rating, 381 reviews

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!

Top guest favorite

Guesthouse in Lake Oswego

4.97 out of 5 average rating, 104 reviews

Secluded Willamette River Apartment in Lake Oswego

Enjoy a private stay full of nature with a river view! Newly remodeled 1 bedroom private apartment secluded and quiet. Apt is completely separate from main house. 10 min wlk to Mary's Woods Ret. Comm, 20 mins to George Rogers Park, 10 more to DT Lake Oswego w/shops, restaurants and theaters. Private, wooded property along the Willamette River. Fully rmld kit. & BR, LR with large 50” Smart TV, fast wifi. Q-bed + twin in sunroom, table/work area + wa/dr below. 8 stair entrance at back.

Top guest favorite

Chalet in Welches

4.97 out of 5 average rating, 479 reviews

The Huckleberry Chalet, private Mt. Hood retreat

Our Mt. Hood chalet has stunning architecture, is located off a quiet road, and backs to a vast and private forest with a small creek. Enjoy multiple indoor levels and explore outdoor decks and beautiful terraced garden spaces and soak in the Oregon Hot Springs hot tub. The home is equipped with fast Wi-Fi and streaming. We’re experienced and responsive hosts that are happy to help make the most your visit, check out our local guide for our favorite restaurants and hikes.

Top guest favorite

Guest suite in Boring

4.96 out of 5 average rating, 494 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

Farm stay in Oregon City

4.91 out of 5 average rating, 467 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!

Top guest favorite

Cottage in Portland

4.92 out of 5 average rating, 426 reviews

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

Guest favorite

Cabin in Milwaukie

4.88 out of 5 average rating, 701 reviews

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Superhost

Farm stay in Sandy

4.89 out of 5 average rating, 636 reviews

Green Acres Private Studio Apartment

Come share our farm adventure. Meet friendly goats, and alpacas, (we sadly lost both of our alpacas to old age this winter.) There are two queen sized beds in a studio apartment with a convenient kitchenette and private bath. There is also a futon chair and a sofa that could accommodate small children. We have an air bed and port-a-crib also available on advanced request. Great ski resorts and hiking trails within 30 miles.

Guest favorite

Cabin in Sandy

4.97 out of 5 average rating, 240 reviews

The Woodlands House

The Woodlands House sits on five acres of an old growth private forest. The home itself is a beautiful 4 bedroom home with two outdoor decks surrounded by towering pine trees. It's the perfect place to get out of the city and disconnect in nature, or to use as your base for all the PNW adventures. It's a quick 30 min drive to Mount hood or the entrance to the Colombia Gorge, and only 45 min from PDX Airport.

Top guest favorite

Home in Mount Hood

4.98 out of 5 average rating, 188 reviews

Peace and Serenity on Mt. Hood-Hike/Bike/Ski/Relax

This 2400 sq. ft. light, bright, modern, private home is nestled in the heart of Mt. Hood in Rhododendron, OR. With a stunning 1.5 acres of artfully landscaped gardens surrounded by forest, you can relax on the 600 sq. ft. deck, or bike, hike, ski and snow shoe the beautiful Mt. Hood forest. Hear the sounds of Clear Creek nearby in this quiet private neighborhood.

Guest favorite

Cabin in Rhododendron

4.92 out of 5 average rating, 388 reviews

Mt. Hood View Burke Cabin

Secluded log cabin with exceptional Mt. Hood and Zig Zag Wilderness views all around. EASY ACCESS, only 3.3 miles from Highway 26. Just moments away from hiking and all the many Mt. Hood area attractions. The cabin is a 700 square-foot rustic log cabin and sleeps 6 comfortably. Camping area available. Pets welcome with $75 per pet fee.