Family-friendly holiday rentals in Oregon

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

The Bag Inn A Hobbit Home

The Bag Inn is a Hobbit Style Home. Filled with comfort and wonder, it will help you step out of the mundane world and retreat to a fantasy world. The Bag Inn features a fire place, walk in shower, and soaker tub. It is 1000 sq ft complete with separate bedroom, large luxurious bath, living and dining space. It sits on 2.5 acres to give you the feel of being out in the country while being only minutes from town. This is a guest home. For more information please read full listing details.

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

The Bluebird House

John Muir once said, "The best place to ride out a storm is in a tree." Enjoy storm watching on the Oregon Coast in a unique way; be warm and cozy inside, feel the sway of the tree, and watch the waves crash below against the famous Samuel Boardman Corridor. Whether you are romatic love birds or a family of adventurers, you will love it! Property is set on seven acres of farm, forest and beach. There are gardens year around, transformed in winter by local fairies and twinkling lights.

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Idyll Ridge - An Unplugged Retreat

Unplug by design at Idyll Ridge, a handcrafted off-grid sanctuary on 9 private acres. Experience total serenity with full-lite glass walls, a massive wood-fired hot tub, and private forest trails. We’ve traded Wi-Fi for absolute peace, but kept the luxury: a chef’s kitchen, a loft with a two-person soaking tub, and a backup generator for total reliability. Whether you’re hiking nearby Saddle Mountain or watching the sunset from the tub, this is the ultimate 2-night forest reset.

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.

Mid-Century Riverfront Cabin - Seclusion Awaits!

Picturesque mid-century cabin...with your own private riverfront! (As seen on Magnolia Network 'Cabin Chronicles'). Boasting a magical view of huge forest trees and 300 feet of river frontage - enjoy a tastefully curated interior with luxury modern appliances & fast wifi. Soak in the incredible views on our expansive deck with a glass of wine, light a campfire on the private pebbled beach. Enjoy fishing/swimming right from your front door! @rivercabaan | rivercabaan . com

Treehouse Glamping Adventure in Sandy, Oregon

The Izer Treehouse is an incredible off-grid retreat. Nestled in a secluded setting amongst the tree-tops overlooking the Bull Run River Canyon, it's the perfect hideaway for couples seeking a romantic escape or BFFs looking for an adventurous getaway. Follow the path and bridge through the trees to your own little treetop oasis. This standalone space rests 30 feet above the forest floor and is perfect for reconnecting with nature and getting away from real-life.

The Royal Scott Double Decker Bus

Our tiny home started life as a commuter bus in Manchester, England, in 1953, then did stints in San Francisco and Mt. St. Helens before finding a home as the Grilled Cheese Grill in Portland. Now it’s been reimagined as a mid century modern-inspired tiny home, with whimsical painting details from one of its former lives and fresh new handmade details that make it a cozy, inspiring stay. Find more on IG @smore.life

Heartland Treehouse

Heartland Treehouse is perched between two massive fir trees overlooking a steep river canyon. Sounds of a nearby waterfall will soothe you to bed at night and gently wake you in the morning. My home is a short walk or drive away and I will be happy to help guide your adventure on Oregon's South Coast. Your treehouse home is secluded, comfortable, and perfect for getting blissed out and recharged.

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.