Guesthouse vacation rentals in Clackamas County

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Top-rated guesthouse rentals in Clackamas County

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Top guest favorite

An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.

Guesthouse in West Linn

4.96 out of 5 average rating, 148 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 favorite

A charming sign reading 'Willow Creek Cottage' is mounted on a yellow wooden wall. Lush greenery surrounds the entrance, adding a touch of nature to the welcoming facade.

Guesthouse in Wilsonville

4.95 out of 5 average rating, 543 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.

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

4.97 out of 5 average rating, 193 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 comfortable seating area is featured, highlighted by a plush couch and a flat-screen TV. A modern shelving unit displays books and decorative items, while a fireplace is positioned below the television. Natural light enters through nearby windows, illuminating the space.

Guesthouse in Sandy

4.98 out of 5 average rating, 167 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 favorite

A welcoming exterior of a two-story home is shown, featuring a large window arrangement and a garage. Lush greenery from a tree extends towards the building, complemented by a neatly landscaped area with potted plants along the driveway.

Guesthouse in Silverton

4.97 out of 5 average rating, 105 reviews

Serene Country Studio

We offer a quiet, private and comfortable 600 sqft studio suite upstairs in a separate structure away from the main house. The room includes a comfortable, king-size bed with Tempur-pedic™ mattress, white cotton sheets and Pendleton™ blankets. A kitchenette with micro-wave, air-fry oven, and dinette are also provided. The studio includes dormers that overlook the family garden, goat barn, and pond. The east windows overlook our back yard, a lily pond and secluded spots to relax and enjoy.

Top guest favorite

The exterior of a white-clad building is illuminated by soft orange light from a sunset. The structure features two garage doors and large windows reflecting the colors of the sky. Surrounding trees and rocky terrain add to the natural setting.

Guesthouse in Silverton

4.99 out of 5 average rating, 380 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 favorite

A serene river view is visible, framed by lush trees and greenery. The clear water reflects the sky, while a gentle wake from a boat creates ripples. A sandy beach area is located in the foreground, alongside a manicured lawn and a fire pit.

Guesthouse in Milwaukie

4.88 out of 5 average rating, 177 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.

Guest favorite

A cozy living area features a comfortable gray couch adorned with decorative pillows. A wooden coffee table sits in front, while two stools stand near a countertop. Sunlight streams through large windows, creating a bright and welcoming ambiance in the open kitchen space.

Guesthouse in Boring

4.91 out of 5 average rating, 196 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

The exterior of the guest house features a wooden facade with large windows, nestled among snow-covered trees. A staircase leads to a balcony area, complemented by satellite dishes. The entrance door is painted green, adding a touch of color to the natural surroundings.

Guesthouse in Rhododendron

4.99 out of 5 average rating, 678 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

The entrance to the studio apartment is framed by vibrant greenery and colorful flower beds. A climbing vine adorns the exterior, while blooming plants in various colors add a welcoming touch to the surrounding landscape. The serene pathway leads to a well-kept entrance.

Guesthouse in Canby

4.95 out of 5 average rating, 212 reviews

Cozy Country Bungalow

*Cozy studio apartment on ten-acre farm. *One queen-size bed *Complete kitchen w/ range, dishwasher, microwave, refrigerator, toaster, and coffeemaker. *Large bathroom, sleeping area with queen bed, living/dining area, and washer and dryer access. *Wireless internet and wall-mounted 40" Smart TV with Netflix. *Relax on your private veranda, or go for a stroll on our 10 acre property. *Enjoy a picnic in the woods. Creek, pond, bridge, & view to enjoy.

Top guest favorite

A welcoming entrance features a white door beneath a cream-colored awning, surrounded by blue siding. Two bistro chairs with woven seats and a small table are positioned on a wooden deck adorned with string lights. Green plants add a lively touch to the space.

Guesthouse in Portland

4.99 out of 5 average rating, 122 reviews

Garden Home Getaway

Welcome to the Garden Home Getaway, your serene retreat in the heart of Portland's Southwest Hills. Our space is designed for luxurious rest and relaxation, while still providing all of the functional and practical comforts of home. An ideal environment for couples and small families to make memories and have the perfect home base for adventurous excursions. We're here to help you curate your stay and find your own slice of Portland.

Top guest favorite

A welcoming cottage exterior features a gray facade with wooden accents. A small patio area is visible, furnished with a table and chairs, surrounded by flower pots. A parked vehicle indicates off-street parking availability, and blooming trees add a touch of natural beauty.

Guesthouse in Silverton

4.99 out of 5 average rating, 477 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.