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Vacation rentals in Clackamas County

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Top-rated vacation rentals in Clackamas County

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A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.

Guesthouse in Oregon City

4.97 out of 5 average rating, 196 reviews

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Top guest favorite

A spacious covered patio area features a large sectional sofa adorned with decorative pillows and a central table. The patio extends seamlessly to an open kitchen area through sliding glass doors, allowing for an airy connection between indoor and outdoor spaces.

4.95 out of 5 average rating, 101 reviews

Secluded mountain luxury home

Escape to our mountain luxury home nestled on 20 wooded acres w/ wild life. Enjoy 2000 sqft in a secluded setting with full views of Mt. Hood. Private 2500 sqft covered patio w/ BBQ. Kitchen and dining that flows through a moveable window wall for indoor/outdoor living. Media room with powered reclining seats w/ tiered theater seating. Laundry. 10 minutes to dining, entertainment, or shopping. 45 minutes to Mt. Hood recreation (skiing, hiking, kayaking). Sofa bed in mediaroom. Bunk bed avail

Top guest favorite

A stunning sunset casts vibrant colors across the sky, creating a backdrop for the tiny house built with natural cedar siding. The silhouette of Mt. Hood is visible in the distance, framed by lush greenery and a pathway leading to the entrance.

Tiny home in Sandy

4.96 out of 5 average rating, 1,192 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 favorite

A panoramic view of snow-capped Mt. Hood is framed by open double doors, providing a striking backdrop to the interior. The rustic dining area features wooden chairs and a table, while the floor is set with dark tiles that contrast with the scenic landscape outside.

Apartment in Sandy

4.99 out of 5 average rating, 400 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 favorite

A canvas platform tent is shown, featuring two beds with cozy bedding arranged inside. Soft lighting is provided by a bedside lamp. The entrance is open, revealing a wooden deck and a green cooler on the ground. Surrounding trees add natural privacy.

4.93 out of 5 average rating, 135 reviews

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.

Top guest favorite

A charming storybook cabin is framed by lush trees, adorned with hanging lights that warm the inviting facade. Flower boxes beneath the windows add color, while a pink door and decorative accents enhance the whimsical aesthetic. An ornamental fence encloses a neat garden area.

Farm stay in Oregon City

4.91 out of 5 average rating, 488 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!

A spacious yurt sits on an island, surrounded by lush greenery and tall trees. String lights are adorned around the tent, adding subtle illumination. A wooden walkway leads to the yurt, with a small stream visible nearby. Colorful bunting adds a festive touch.

Yurt in Estacada

4.95 out of 5 average rating, 450 reviews

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.

A serene garden scene features a waterfall cascading over natural stone, surrounded by lush greenery and colorful flowers. A small pond is visible at the base of the waterfall, complemented by a tranquil statue. Various plants add vibrant textures and colors throughout the landscape.

Guest suite in Damascus

4.92 out of 5 average rating, 610 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.

Top guest favorite

The vintage cabin presents a charming exterior with a grey-brown wooden facade and a sloping metal roof. Hand-carved stairs lead to a welcoming porch adorned with red accents. Lush greenery surrounds the cabin, with tall trees providing a serene backdrop.

Cabin in Clackamas County

4.9 out of 5 average rating, 273 reviews

Historic Steiner log cabin on Mt Hood

Stay in one of the most charming vintage cabins on Mt. Hood, hand-built in 1930 by Oregon's famous cabin builder, Henry Steiner. Experience authentic cabin life as you cozy up with blanket and book by the fire, cook delicious meals, or fall asleep to the soft patter of rain on the roof. This one-of-a-kind cabin is truly a historic treasure. Every detail has been lovingly restored, featuring beautiful log walls, sleeping loft, clawfoot tub, and stone fireplace.

A modern retreat structure is nestled among towering trees and lush ferns. Wooden exterior panels contrast with large glass windows, allowing for views of the surrounding forest. Smoke gently wafts from the chimney, indicating warmth within the cabin.

Tiny home in Sandy

4.97 out of 5 average rating, 281 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 favorite

The sleeping area features a queen bed with a patchwork quilt, flanked by two bedside lamps. An array of vintage posters adorns the walls, creating a vibrant atmosphere. A small reading chair sits next to a desk in the corner, enhancing the cozy and functional space.

Place to stay in Estacada

4.99 out of 5 average rating, 287 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 favorite

A cozy cabin interior features a wood stove providing warmth. A small kitchenette with a mini fridge is visible, alongside a dining table with two chairs. The wooden floor adds warmth, while a large window allows natural light to illuminate the space.

Guesthouse in Beavercreek

4.97 out of 5 average rating, 268 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.

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Popular amenities for Clackamas County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Clackamas County

Top guest favorite

A hot tub is situated on a deck, surrounded by serene views of rolling hills at dusk. String lights hang gently above, providing soft illumination. Green glow from the hot tub reflects off the water, creating a calming atmosphere as twilight descends.

Tiny home in Estacada

4.99 out of 5 average rating, 78 reviews

Luxury Tiny Home with a view!

Top guest favorite

The cabin is surrounded by towering trees, offering a sense of seclusion. A spacious deck is equipped with an inviting hot tub and seating area. A stone fire pit with black Adirondack chairs creates a cozy gathering space, all illuminated by string lights as the sun sets.

Cabin in Mount Hood Village

5 out of 5 average rating, 60 reviews

Barlow Haus

Top guest favorite

An outdoor patio setup is illuminated by string lights, creating a warm ambiance. A cozy seating arrangement includes two armchairs and a small table near a fire pit. A jacuzzi is present in the background, surrounded by greenery, enhancing the tranquil outdoor setting.

Home in Scotts Mills

5 out of 5 average rating, 34 reviews

Abiqua Couple Getaway

Top guest favorite

An inviting living area features a high arched wooden ceiling, accented by a stone fireplace. Large windows provide ample natural light and views of the outdoors. Comfortable seating is arranged around a stylish coffee table, with a globe and decorative elements adding character.

4.99 out of 5 average rating, 96 reviews

Arched Cabin with sauna on the Sandy River

Top guest favorite

A single-story home is presented, featuring a welcoming front porch with a ramp. Flower boxes add color to the building's exterior, which is surrounded by a low stone wall and wooden picket fencing. Bright blue skies create a clear and sunny atmosphere.

Home in Oregon City

5 out of 5 average rating, 35 reviews

Rural Country Home

A covered deck offers a firepit surrounded by two reclining chairs. The expansive view reveals a lush, green lawn and distant trees under a vibrant sunset sky, creating an inviting space for relaxation.

Guesthouse in Sandy

4.97 out of 5 average rating, 98 reviews

Come Escape @ Mount Hood Retreat

Top guest favorite

A modern kitchen features deep green cabinetry and a spacious countertop. A round wooden dining table is set with white plates and glasses, complemented by a delicate floral arrangement. A woven pendant light hangs above, creating a warm and inviting atmosphere.

Guesthouse in Molalla

5 out of 5 average rating, 45 reviews

A quiet retreat amongst the oaks

Top guest favorite

A cozy, round cabin is nestled among tall trees, featuring a distinctive moss-covered roof. The front entrance is framed by vibrant red doors, with natural leaves scattered across the ground. Potted plants are positioned near the base, adding touches of greenery.

4.97 out of 5 average rating, 69 reviews

The Story House

Destinations to explore