Family-friendly holiday rentals in Clackamas County

Mt. Hood Autumn Getaway: 1BR Apartment

Welcome to your private one-bedroom apartment in Welches, Oregon! Just 18 minutes from Skibowl and 30 minutes from Timberline and Mt. Hood Meadows, this cozy retreat is perfect for two guests (or three with a child under 12). Located on the first floor of our home, the apartment has high-speed internet and a comfy space to unwind after adventure. Since we live upstairs, you may occasionally hear footsteps. Pets: Due to severe allergies, no animals, sorry! Free parking on-site | STR798-22

Heated Glamping tent, Action sports- Site 3

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.

Forest island

Glamping at its finest !!!!!! Come enjoy our Private forest island retreat on our 22 acre working farm . Relax and take in the fresh air without the hassle of having to pack up all your camping equipment. The spacious yurt can accommodate up to 4 people with a queen size bed and a 2 person pull out cot. This private yurt is on a island on our land surrounded by the water and trees. We also have kayak for rental upon request to use at the surrounding lakes and river.

Foxglove Farm Private Guest Suite

Enjoy a stay in a ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

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.

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.

Green Acres Private Studio Apartment

Come share our beautiful five acres. There are two queen sized beds in a studio apartment with a convenient kitchenette and private bath. There is also a futon chair and a sofa that could accommodate small children. Great ski resorts and hiking trails within 30 miles. Put your phone on WiFi calling for best service. WiFi is Listed on the chalkboard along with other notifications.

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.