Family-friendly vacation rentals in Gladstone

Forested Hygge House Getaway

Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Some uneven paths and slip hazards are present

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.

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Gladstone Garden Retreat

Lovely updated bungalow, private & quiet garden retreat in old Gladstone home, walking distance to Clackamas River. Gated yard with garden, grill, outdoor dining, east facing windows, private keyless entrance, off street parking. Tons of natural light; beautifully decorated; AC, HDTV, Wi-Fi, Cable TV with movie channels; Queen beds; designer appliances for gourmet meals; rock fireplace w/ gas, soaking tub upstairs, updated shower downstairs; washer & dryer. Pet friendly patio w/ doggie door.

The River House - Waterfront Retreat w/Fireplace

Experience the serenity of riverside living in our private, enchanting retreat nestled on the tranquil banks of the Clackamas River. This guest suite offers 1500 square feet of living space, boasting a private entrance and a spacious deck that grants breathtaking views of both the serene pond and the majestic river. Step inside to discover a haven of comfort and elegance. The gourmet kitchen features SS appliances, sleek granite countertops, and is fully stocked for your culinary needs.

The Wee Humble Cottage

Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

Spacious and Private Place with a BIG Yard

Private and quiet space with over 800sq/ft of living space. Big living room and fully stocked kitchen. Relax in a queen sized bed next to an indoor fireplace. Kick back in the open concept space. Plenty of natural sunlight, separate key code entrance, and a big gated yard. 15 min to downtown Portland. Plenty of parking, close to the river and next door to a park which has tennis and basketball courts and is wonderful to walk and great for dogs. Can’t wait for your Portland

Blue Heron Sanctuary · Private Riverfront Cottage

Rates vary by season and length of stay. Final pricing is displayed when dates are selected. Tucked along the Willamette River, this thoughtfully restored cottage offers a rare blend of nature, comfort, and calm. Enjoy private river access, garden views, a well-equipped kitchen, curated sleep comforts, and fast fiber internet. Walk to parks and trails, unwind by the fire pit, or work peacefully surrounded by trees—an ideal retreat for rest, creativity, or extended stays.

Oak Grove Easy-Centrally located w/King Bed

Welcome to this updated and comfortable, light filled home in the Oak Grove neighborhood of Portland. A short distance to the river, downtown, parks, restaurants and all things Portland-make this a perfect vacation space for your family and guests. We put a lot of love in to designing the interior to be stylish, yet comfortable and seamless to ensure you feel right at home. Ample space in our park-like backyard to relax , entertain or play a summer game of corn hole!

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! Please be advised that beginning Dec19, 2025, construction has begun on three homes behind our cottage. Work can begin at 7:00AM-7:00PM Mon-Fri., 9:00AM-5:00PM Sat.-Sun. There could be noise during those hours, it's out of our control.

Cozy Modern Family 3Bd Oasis

Centrally located in West Linn. Safe, Clean, Great for Families! Minutes from Award Winning Wineries, Lake Oswego, Oregon City, and Downtown! This home is minutes walk North Willamette Park! Stylish, comfortable, and clean with all the amenities you need to make your vacation or business trip a success. Property is a unit in a newly renovated duplex. Enjoy the private fenced back yard and patio / common yard with picnic tables / Free private parking!

Evergreen Escape - Relaxing South Metro Studio

Recently updated pricing and NOW NO CLEANING FEES! Quiet basement studio with efficiency kitchen and full bath with rain shower. Located a short distance south of downtown Portland, West Linn is a quiet suburb on the Willamette River. Our home is walkable to a great pub, groceries and other restaurants. This listing includes a lofted queen bed with charming barn door for privacy.