Family-friendly holiday rentals in Clackamas County

Park Cottage

This charming guesthouse is tucked away in a park-like setting near the entrance to the Willamette Valley Wine Country. This very spacious studio offers a warm and cozy space with king size bed and a comfy day bed with a pull out trundle. Also a very roomy living room area with tv for streaming ( Roku/Netflix installed ) and fire place. Enjoy light meals or snacks in the kitchenette with a full fridge , microwave,toaster, coffee maker and all kitchen utensils. Beautiful outside surroundings.

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.

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.

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.

Luxury Tiny Home with a view!

Escape to peace and tranquility at Tiny Timber, a cozy retreat set on a scenic 65-acre Christmas tree and timber farm. Take in sweeping Cascade views, unwind with luxurious amenities, and enjoy your own private oasis. Start or end your day with a soak in the private hot tub under the open sky. Ideally located near the Clackamas River, Mt. Hood National Forest, and greater Portland, Tiny Timber is your gateway to adventure, exploration, and true relaxation.

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!

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.

Buena Vista Guest House.

Take it easy at this tranquil getaway. Stay at our beautiful lavender farm located in the rolling hills 8 miles south of Silverton Oregon. Our guesthouse is a private, quiet, and cozy get-away that is surrounded by beautiful views of the Willamette Valley and coastal range. Enjoy the quiet evenings on the private patio enjoying the amazing views! Pictures do not do it justice. This is a hidden gem.

Heated Glamping tent #1 on Mt. Hood

Stay in a cozy canvas tent tucked in the woods on the grounds of a legendary action sports destination at the base of Mt. Hood. With year-round lift-accessed snow and epic bike trails just minutes away, plus limited access to private skate parks and a full fitness center on site, this is the ultimate basecamp for riders, skaters, adventurers, or anyone craving fresh mountain air.

WanderingWoods A-Frame Cabin

Enjoy the comforts of home in this cute and cozy A-Frame cabin, which offers both privacy and convenience to nearby activities! Located near The Resort at the Mountain, you're only 20 miles to Timberline Lodge and all of Mt. Hood's splendor. The Upper and Lower Salmon River Trailheads are just up the road, and a multitude of other hiking opportunities nearby.

Creekside Cozy Cabin

Nestled among tall cedars, you'll find the Creekside Cozy Cabin a perfect place to relax and enjoy its calm surroundings. While there are neighbors on both sides of the cabin, you still get that country feel away from the city. We are 20 miles from PDX Airport and 21 miles from Downtown Portland, but the drive out to the cabin is worth every mile.

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.