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 Oregon City

4.98 out of 5 average rating, 164 reviews

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Discover our serene Clackamas Riverfront Guest House – a peaceful riverside getaway. This stylish retreat features a private hot tub and sauna, blending modern comforts with rustic charm. Unwind by the fireplace, savor river views, and embrace nature's beauty. Our river facing backyard provides access to the river where you can fish for salmon, steelhead, go kayaking, rafting and enjoy water adventures. Perfect spot for romantic escapes or solo rejuvenation. Experience luxury nestled in nature.

Top Guest favourite

Apartment in Oregon City

4.99 out of 5 average rating, 104 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, 442 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

4.98 out of 5 average rating, 270 reviews

The Woodlands Hideout

The Woodlands Hideout is a small intentional retreat space, featured in Dwell. Designed and created with so much love, and with the hope that guests could immerse in the beauty of the natural world, but still offer some cozy and more essential comforts. You will love the large windows, the wood stove, and the calming aesthetic. 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.

Guest favourite

Place to stay in Woodburn

4.91 out of 5 average rating, 253 reviews

A-Frame Cabin: Picturesque view and cozy interior

Minutes from the outlet mall, a peaceful and cozy A-Frame, nestled in the trees overlooking a rippling creek. The stairs to the loft lead to a room where there is a comfortable queen-size bed and television. The downstairs area has a fully-stocked kitchen, dining area and living area with lots of windows to enjoy the view. There is also patio with a table and chairs and propane grill where you can sit and enjoy the view of the pasture and water, with beautiful trees scattered about.

Superhost

Home in Rhododendron

4.86 out of 5 average rating, 118 reviews

Little bear creekside cabin

Our cabin, nestled in the Mt. Hood National Forest is the perfect backdrop for any romantic getaway, family vacation, or quiet solitude. Hot tub with your love one under a canopy of trees, explore the nature and wildlife, or even local dining and attractions. Whether you love to hike, stay in with a movie or BBQ, this cabin has it all for you. Make the most of your time away by spending it here. Pet friendly cabin Bear creek cabin is registered with Clackamas county, # 850-23

Top Guest favourite

Guest suite in Boring

4.96 out of 5 average rating, 491 reviews

Tiny Private Studio near Sandy, Oregon

Located between Mt. Hood and the Columbia Gorge! Cozy private studio, with a separate entrance on 2 quiet acres. This small studio has a comfortable queen bed with luxury linens throughout. A tiny kitchenette supplied with coffee, organic half and half, an assortment of tea, bottled water, and a few snacks. Wifi and YouTubeTV provided. Grocery stores, restaurants, movie theater, gym, and hiking trails just to name a few amenities all within 1 to 3 miles of our home.

Guest favourite

Farm stay in Oregon City

4.91 out of 5 average rating, 463 reviews

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

Top Guest favourite

Apartment in Hubbard

4.97 out of 5 average rating, 171 reviews

Peace and Quiet on a Farm in the Country

Enjoy the peace and quiet of the country in a 2 bedroom apartment on a working berry farm. The apartment is located in a separate building away from the main house so there is lots of privacy as well. You can even pick your own marionberries and blueberries when in season. There are also a number of u-pick farms and farm stands in the area. When the restrictions for COVID-19 are lifted, you can be assured that the space will be thoroughly cleaned and disinfected.

Top Guest favourite

Guest suite in Milwaukie

4.99 out of 5 average rating, 393 reviews

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

Top Guest favourite

Place to stay in Estacada

4.99 out of 5 average rating, 260 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...

Top Guest favourite

Farm stay in Oregon City

4.96 out of 5 average rating, 291 reviews

Farm Charm: 1000sq ft private studio in rural area

With unique vintage decor, this comfortable studio offers modern amenities in a peaceful country setting. The space has a private keypad entrance & 16 stairs (sorry, no elevator) to the guest studio attached to our home. Our friendly golden retriever Ollie will gladly greet you. Groceries & highway access are a mere 3 miles away. Portland is a short easy drive from our quiet country home.