Holiday houses in Clackamas County

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Top-rated holiday rentals in Clackamas County

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Top Guest favourite

Guesthouse in West Linn

4.96 out of 5 average rating, 146 reviews

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

Top Guest favourite

Apartment in Oregon City

4.99 out of 5 average rating, 115 reviews

Private, comfy & cozy apartment in OC neighborhood

Enjoy a comfortable stay in our private (above garage) apartment. Safe, quiet and family friendly neighborhood with walkable distance to 2 parks. 10 minutes to the I-205 freeway and 25 min to PDX airport. Within 2 hours of the coast or Mt. Hood. Oregon City has several fun things to offer near by :: Food trucks, restaurants, brew pubs, shopping, coffee shops, free OC elevator with amazing views, End of the Oregon Trail museum, walking trails, Clackamas and Willamette rivers and so much more!

Guest favourite

Guest suite in Estacada

4.75 out of 5 average rating, 452 reviews

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.

Guest favourite

Tiny home in Sandy

4.96 out of 5 average rating, 1,183 reviews

Mt Hood View Tiny House

Sandy's first and only Tiny House! Although this home is located just a mile from Hwy 26 within Sandy's city limits, it's located on a private 23 acres, so you'll feel completely secluded. This makes it the perfect place to stay while visiting the Mt. Hood area. The tiny house was built to capture the amazing view of Mt. Hood. The home was designed around a moving window wall system that completely opens to the outdoors allowing for one of the best views of Mt. Hood. We hope you enjoy!!!

Top Guest favourite

Guesthouse in Sandy

4.98 out of 5 average rating, 161 reviews

The Sandy Sanctuary

Ready for a break? Want a weekend getaway, a lot closer to recreation? The Sandy Sanctuary is your spot! We've designed this studio to be a space where you can unwind, surrounded by giant evergreens on the outside, and filled with delightful offerings on the inside. 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 and coffee, as well as stunning trails!

Top Guest favourite

Apartment in Sandy

4.99 out of 5 average rating, 393 reviews

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!

Top Guest favourite

Guesthouse in Silverton

4.99 out of 5 average rating, 375 reviews

The Rock Tree House - A place to unwind and renew.

Welcome to the Rock Tree House! This studio apartment is the perfect get-away retreat for the outdoor enthusiast: 20 minutes to Silver Falls State Park, 2 miles from the quaint downtown Silverton, and well within driving distance of all the Willamette Valley has to offer. Enjoy your morning coffee on the private outdoor deck surrounded by beautiful trees and abundant wildlife. Our home is a safe space for all people. We welcome guests of all races, faiths, genders, and sexual orientations.

Guest favourite

Guest suite in Damascus

4.92 out of 5 average rating, 607 reviews

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.

Guest favourite

Tiny home in Sandy

4.97 out of 5 average rating, 278 reviews

The Woodlands Hideout

The Woodlands Hideout is a small intentional semi-offgrid retreat space, featured on Dwell. It was designed and built by Further Society and created to allow guests to immerse in the beauty of the natural world, but still offer some cozy and more essential comforts. Although the footprint of the space is small, we designed the experience to be outward focussed, so it feels very expansive with the towering pine trees in view.

Top Guest favourite

Place to stay in Estacada

4.99 out of 5 average rating, 276 reviews

"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...

Guest favourite

Guesthouse in Beavercreek

4.98 out of 5 average rating, 257 reviews

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.

Top Guest favourite

Guest suite in West Linn

4.99 out of 5 average rating, 271 reviews

Private Casita in Historic Willamette

Located in the highly desired Historic Willamette district of West Linn, this newly-built casita provides a private bedroom and bathroom with its own entrance. Enjoy walking to restaurants, coffee shops, beer pubs, wine bars, and retail shopping all within several blocks, or take a stroll to the Willamette Park just six blocks south.