Family-friendly holiday rentals in Oregon City

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.

Lovely Historic Apartment in the Heart of OC

You'll love my place because of it's unbeatable location (and walkable distance) to everything Oregon City has to offer: food carts, brew pubs, restaurants, library, public elevator, shopping, cafes, parks, walking trails, family friendly activities, Willamette River, Oregon City TriMet Transit Center, Amtrak Train station, etc. Only 5 minutes drive to I-205, 25 minutes to downtown Portland, and 30 minutes to PDX airport! Inside has everything you need including a full kitchen and washer/dryer!

Private, comfy & cozy apartment in OC neighborhood

Enjoy a comfortable stay in our private (above garage) apartment. Safe, quiet and family friendly neighborhood with walkable distance to 2 parks. 10 minutes to the I-205 freeway and 25 min to PDX airport. Within 2 hours of the coast or Mt. Hood. Oregon City has several fun things to offer near by :: Food trucks, restaurants, brew pubs, shopping, coffee shops, free OC elevator with amazing views, End of the Oregon Trail museum, walking trails, Clackamas and Willamette rivers and so much more!

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.

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.

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.

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!

Stargazing Glamping | Swim | Oasis

Sip a cup of coffee on your private deck overlooking the forest. Swim in our natural spring-fed little lake, canoe, or read a book in a hammock. Make memories in nature at The Hideout. With a Lotus Belle Tent surrounded by wildlife and stars galore, our magical oasis will be your unforgettable getaway. *we do not have a zipline for public use - this is not included in your rental and not available for use*

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.

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.

Private Deck · Dual Showers · Pets OK · OR City

Cozy ADU retreat in Oregon City with a private deck, dual shower heads, and room for 4. About 30 minutes from downtown Portland via I-205, close to local dining, shops, and the historic Willamette Falls. Free parking, fully equipped kitchen, queen bed plus bunk nook. Perfect for couples, small groups, or a Portland-area getaway.