Guesthouse vacation rentals in Clackamas County

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Top-rated guesthouse rentals in Clackamas County

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Top guest favorite

A wooden sauna in a barrel shape is illuminated warmly from within, revealing a serene interior. Tall evergreen trees rise in the background, contrasting against the twilight sky as a soft glow emanates from the open door, inviting relaxation.

Guesthouse in Sandy

4.93 out of 5 average rating, 241 reviews

Sauna! Free daily HOUR w/2 nite stay!

Our large(850sq.ft)studio is urban modern,has a touch of rustic charm, and is comfortable and cozy.We sit on a 5 acre homestead just 2 miles from a small town.The studio sits 35 ft off the back corner of main house.Sunrises are spectacular here and so is the wide open,starry night sky.We are located centrally between Mt. Hood,the Columbia Gorge&Portland.We offer a great place to base yourself to explore all the great sights nearby or just to stay on the quiet country property and soak it all in.

Top guest favorite

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

4.99 out of 5 average rating, 151 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 favorite

A winding gravel path stretches through a lush landscape, bordered by trees and vibrant pink blossoms. Sunlight filters through the branches, casting gentle shadows on the ground. A fence lines the path, enhancing the tranquil, natural setting.

Guesthouse in Wilsonville

4.95 out of 5 average rating, 508 reviews

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. Great location - 20 minutes to Portland, 25 minutes to Oregon Wine Country, 90 minutes to the coast and five minutes from I-5 and Wilsonville. Bedroom with comfy pillow top queen bed. Breakfast nook with refrigerator, microwave and Keurig coffee maker. Direct TV and WiFi. **Please be assured that we continue to take all steps necessary to sanitize and air the cottage before your visit.

Top guest favorite

A welcoming entrance features a black front door framed by sleek, modern architectural accents. Flanking the door are small, manicured bushes and potted plants, enhancing the inviting outdoor space. The pathway is lined with gravel, leading into a serene, park-like setting.

Guesthouse in Beaverton

4.99 out of 5 average rating, 298 reviews

Park Cottage

This charming guesthouse is tucked away in a park-like setting near the entrance to the Willamette Valley Wine Country. This very spacious studio offers a warm and cozy space with king size bed and a comfy day bed with a pull out trundle. Also a very roomy living room area with tv for streaming ( Roku/Netflix installed ) and fire place. Enjoy light meals or snacks in the kitchenette with a full fridge , microwave,toaster, coffee maker and all kitchen utensils. Beautiful outside surroundings.

Guest favorite

A wooden deck overlooks the river, featuring a round table surrounded by four chairs. Lush greenery can be seen across the water, with trees lining the shore under a partly cloudy sky.

Guesthouse in Milwaukie

4.87 out of 5 average rating, 174 reviews

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

Superhost

Guesthouse in Damascus

4.9 out of 5 average rating, 124 reviews

Hygge House-luxurious secluded 3BR guesthouse

The Hygge House PNW is a place to unwind, get cozy and enjoy the company of those you love. Cuddle up with a cup of tea or a good book and enjoy a restful retreat. Enjoy country vibes while being moments away from Happy Valley City Center. Whether you're in town visiting friends and family or looking to experience everything Portland has to offer, the Hygge House has you covered. We hope you enjoy your time spent here and leave feeling relaxed and more connected with the ones you love.

Top guest favorite

Guesthouse in Gladstone

4.96 out of 5 average rating, 118 reviews

The River House - Waterfront Retreat w/Fireplace

Experience the serenity of riverside living in our private, enchanting retreat nestled on the tranquil banks of the Clackamas River. This guest suite offers 1500 square feet of living space, boasting a private entrance and a spacious deck that grants breathtaking views of both the serene pond and the majestic river. Step inside to discover a haven of comfort and elegance. The gourmet kitchen features SS appliances, sleek granite countertops, and is fully stocked for your culinary needs.

Guest favorite

A well-maintained green lawn is framed by carefully pruned shrubs and trees. A variety of foliage adds texture, with vibrant accents from surrounding plants. A neat path leads through the landscape, creating a serene outdoor space that enhances the guest house's private setting.

Guesthouse in Boring

4.91 out of 5 average rating, 183 reviews

Boring Bungalow /1 bedroom guesthouse with kitchen

Private and quaint one bedroom one bathroom guest house in beautiful Boring Oregon. Centrally located between beautiful Mt Hood recreation area, breathtaking Columbia River Gorge and the stunning Oregon Coast. You have a private entrance with keyless entry, a comfortable living area and well appointed kitchen. Free on site parking with room for boat and trailer if needed. All linens are provided, as well as a starter supply of toiletries, coffee and tea. STR784-22

Top guest favorite

A flowing river runs over smooth rocks, with a snow-capped mountain towering in the background. Tall trees frame the scene, highlighting the natural beauty of the surrounding wilderness under a clear blue sky.

Guesthouse in Rhododendron

4.99 out of 5 average rating, 642 reviews

The Bear's Den, studio with kitchen and pond/creek

Our wonderful guest house is a cozy studio with a queen bed, kitchen, sofa, and dining table in one large room. There is a bathroom with shower. This is a second floor apartment over the detached garage, we live in the main house next door. The property is very secluded well off the road with no other houses nearby and borders the National Forest. Enjoy the spring fed pond in the front yard, a hike along the Sandy river, or a 15 min drive to ski resorts.

Top guest favorite

A scenic view of a dock extending over calm water, surrounded by trees and reflecting the structures in the background. The dock features two lounge chairs and a kayak, creating a peaceful outdoor setting near the river.

Guesthouse in Milwaukie

4.99 out of 5 average rating, 336 reviews

River Forest Guest House, All new+Riverfront Patio

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

Superhost

A wooden staircase is depicted leading to a raised deck area, surrounded by a fenced yard for privacy. The patio features paved stone flooring, creating an inviting outdoor space with gravel and greenery from nearby trees.

Guesthouse in Oregon City

4.89 out of 5 average rating, 227 reviews

Modern Tiny Home | Near DT OC|Dual Shower Heads

This tiny-home makes for a perfect family stop-over or extended stay while visiting Portland and surrounding areas. Close access to the 205 freeway as well as Abernethy Center(Wedding Venue). Visit the Oregon Trail Museum, and historic downtown Oregon City. Free parking on premises, fully equipped kitchen, set in a quiet peaceful neighborhood Great for short or long term stays as well as traveling nurses.

Top guest favorite

A sheltered gazebo features a round table with four high-backed chairs, complemented by hanging flower baskets. A concrete patio surrounds the structure, and a wooden privacy fence creates a secluded atmosphere. Soft lighting adds a warm touch to the outdoor space.

Guesthouse in Silverton

4.99 out of 5 average rating, 458 reviews

Cozy Cottage close to town

Self-contained private cottage within walking distance of historic downtown Silverton. Just across the street from the YMCA pool (about a 5 minute walk). Short drive away from Silver Falls State Park and also the Oregon Garden. The Willamette Valley wine country is less than an hours drive and the beautiful Oregon coast a little over an hour. Oregon's capital, Salem can be reached in about 15 minutes.