Family-friendly holiday rentals in Clackamas County

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.

Heated Glamping tent on Mt. Hood - Site 1

Nestled at the foot of Mt. Hood and its year-round lift-accessible snow, these indulgent canvas platform tents place you on the campus of one of the world's premiere action sports destinations. With Sandy Ridge bike trails within a mile and over 1-acre of skateboard park, there is something for everyone. Your luxurious tent site is one of ten featuring a communal campfire and picnic tables. At various times, you'll have access to our famous private skate parks, trails, and fitness center.

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

"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...

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.

Modern Townhouse

Newly built gated Modern Townhouse. Beautiful and scenic drive to Timberline Lodge / Mt. Hood Ski Bowl. 25 minute drive to downtown Portland. 15 minute drive to Clackamas Town Center. Minutes away from 172nd / Sunnyside shopping center and restsurants. Close drive to Multnomah Falls. Close drive to Vista House view point. Lots of hikes and trails nearby.

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.