Family-friendly holiday rentals in Clackamas County

Oswego Empty Nest

The Oswego Empty Nest is a newly remodeled, cozy, one bedroom unit located in Lake Oswego with a private entrance and 500 sq ft of living space. Prepare your own meals in the beautiful full kitchen. Relax, work or entertain yourself in the living space with a large TV with Roku or rest in the quiet comfortable bedroom with an en suite bathroom. Easy access to restaurants, New Seasons, Columbia Outlet, and hiking trails all within walking distance. Close to downtown and quick airport access.

Tiny House in a quiet oak grove

Tiny House Guest Cottage one mile off 213 near Marquam. Remote, yet accessible. 10 minutes from Mt. Angel and Molalla. 15 minutes from Silverton. 18 minutes from Oregon Garden. Loft with King size bed and luxurious sheets. Two sofas downstairs can be converted into beds. Not suitable for children. Sit on the back patio in the evening and listen to owls, coyotes, frogs, and crickets. Dozens of species of birds. I am proud of the reviews guests have left; please read them for more info.

Mt Hood View Tiny House!

Sandy’s first and only Tiny House! Located just one mile from Hwy 26, this unique tiny home sits on 23 acres, offering a peaceful, private setting with easy access to Mt. Hood adventures. The tiny house has its own space and stunning Mt. Hood views, with our main home visible but not impacting your privacy. Designed around a custom moving window wall system, it opens fully to the outdoors, bringing the mountain right into your stay for unforgettable sunrises, sunsets, and true Mt. Hood magic.

Little Explorer - The perfect mountain escape.

Located near the end of a quiet dead end road in Welches, Oregon. Short path to Sandy River. Easy access to HWY 26 and only 15 minutes to Government Camp or Sandy Ridge mountain biking. Enjoy the relaxing surroundings while staying in a newly renovated cabin with all the comforts of home. 2 night min. stay seasonally/Fri/Sat but possibly accept a 1 night stay...just ask. Sleeps 4 in beds. Anymore you provide bedding and/or air mattresses. Check out our Instagram @ littleexplorer_oregon

Serene Country Studio

We offer a quiet, private and comfortable 600 sqft studio suite upstairs in a separate structure away from the main house. The room includes a comfortable, king-size bed with Tempur-pedic™ mattress, white cotton sheets and Pendleton™ blankets. A kitchenette with micro-wave, air-fry oven, and dinette are also provided. The studio includes dormers that overlook the family garden, goat barn, and pond. The east windows overlook our back yard, a lily pond and secluded spots to relax and enjoy.

Lewis and Clark Hide-A-Way Apartment

Private entrance apartment in Southwest Portland near Lewis & Clark College, OHSU, Multnomah Village and Hillsdale. Large living room, full size kitchen. Extremely quite bedroom with queen bed, single roll away bed and pak-n-play bed available. Large outdoor patio space with barbeque, play structure for children, fire pit and fenced yard. Quiet neighborhood, walking distance to Moonlight grill, Chez Jose Mexican, Tokyroll sushi, Tryon creek sports bar. Walking distance to Tryon Creek.

Arched Cabin with sauna on the Sandy River

Welcome to our stunning two-bedroom, two-bath arched cabin nestled along the Sandy River. Enjoy direct access to the river, where you can bask in the natural beauty of the surroundings and a view of Mt. Hood. The open concept living area boasts large windows that frame the breathtaking river views, creating an inviting ambiance that's perfect for relaxing. Indulge in a the barrel sauna with panoramic river vista. The cabin is close to endless activities up and around Mt. Hood.

Sandy Sanctuary

Ready for a break? Want a cozy getaway, closer to recreation? Sandy Sanctuary is your spot! Surrounded by evergreens on the outside, and filled with delightful offerings on the inside: puzzles, books, a fireplace and premium linens. Whether you're a weekend warrior, or just want a break from the grind, we think you'll find this a blissful place to rest your head. Located on the edge of Sandy, it's walkable to food carts, coffee, and stunning trails!

Burke Cabin | Mt. Hood View | Private Acreage

Cozy 700 sq. ft. rustic log cabin with stunning views of Mt. Hood and Zigzag Wilderness. Just 3.3 miles from Highway 26, a perfect mix of privacy and easy access year-round. The cabin sleeps up to six guests comfortably. With hiking trails, ski resorts, and Mt. Hood attractions just minutes away, adventure is never far. Pets are welcome with a $75 fee per pet, so the whole family can enjoy this peaceful mountain retreat!

Little House On The Mountain — Spacious Tiny House

Relax and unwind in our custom built, one-of-kind cabin. The cabin is nestled up on a forested hill above our main cabin. It's sits on 4 acres of private wooded land, bordering Mt. Hood National Forest Land. A perfect getaway for couples looking to spend a romantic weekend in the woods or a home-base for those who are here to enjoy everything Mt. Hood has to offer. Hiking, fishing, skiing are only minutes away!

"Worth 10 stars" Lucky Dawg Hideaway

Our LUCKY DAWG Hideaway is a well-equipped unique comfortable space with a queen bed, small kitchen, laundry area and bathroom. The cozy outdoor patio adds to your living area. Estacada is centrally located (abt an hour drive) to both downtown Portland and Mt Hood for all-year skiing and world-class hiking...Plus, we're about a 2.5 hour drive to either the beach or the high desert of central Oregon...

Signal House – Light Up The Portal

Signal House is an immersive art home from The Book of Houses in Pudding Heroes – a living chapter of the story. It is an overnight experiential stay, for travelers looking to jump off to the next dimension. Our 3 room home's highlight is the fully mirrored experience with sound /mood lighting for play & sleep. We have a cat meme lounging experience in the media room. 15 minutes from Portland on I-5.