Guesthouse holiday rentals in Clackamas County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Clackamas County guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Aurora
4.98 out of 5 average rating, 63 reviews

Chayah House at Moriah Hills

LeahRating, 5 stars6 months ago
This place was perfect. Large deck overlooked nice woods, a pond, and you could see Mt. Hood in the distance. Living room was big and comfortable. Kitchen had plenty of dishes, lots of pots, and even small appliances to making cooking easy. Parking was right there. Every thing was new and in working order. The decor was mountain rustic cool. My favorite thing was that the living room and kitchen were arranged to make the most of the view. Warm throws for coziness, nice colors in the rugs and walls. Lots of attention to comfort and detail. Seemed in the middle of nowhere but actually close to stores and amenities. Very quiet and peaceful.
Guest favourite
Guesthouse in Oregon City
4.93 out of 5 average rating, 128 reviews

Andrew's House - Guest Suite

Anne MarieRating, 5 stars6 months ago
We chose Kim and Pat’s place over the closest hotel in the area where we were attending a family wedding and are so glad we did. Their place was private, charming, and well equipped and the cost was about the same as the local hotel. It felt like we really got to enjoy a weekend getaway in spite of being out at family activities for most of the time. Would happily stay again.
Guest favourite
Guesthouse in Portland
4.89 out of 5 average rating, 230 reviews

Sellwood Luxury Studio Home

JohnRating, 5 stars4 weeks ago
We loved our stay here in this beautiful neighborhood. Was perfect for our needs!
Top Guest favourite
Guesthouse in Lake Oswego
4.97 out of 5 average rating, 99 reviews

Secluded Willamette River Apartment in Lake Oswego

AdrienneRating, 5 stars1 week ago
What a great spot in a beautiful location! Very peaceful, homey and the perfect place if you like walks. Would love to stay again on my next visit!
Guest favourite
Guesthouse in Mount Hood Village
4.96 out of 5 average rating, 191 reviews

Dancing Bear Cottage

CharliRating, 5 stars1 month ago
Lovely place allows easy access to the snow. Within 1/2 hour we were at Trillium Lake, closer yet to Government Camp! Lovely peaceful surrounding.
Superhost
Guesthouse in Lake Oswego
4.79 out of 5 average rating, 82 reviews

Cottage on the Creek in Lake Oswego

JeffRating, 5 stars4 months ago
We picked the location because it was close to my mom's house, where our family had gathered for the holidays so we did not spend a lot of time in the cabin. The kitchen was well equipped and there was on site laundry - always a bonus! As it rained the entire time we were there, we did not have the opportunity to enjoy the deck and back yard, which would have been a lovely place in the Portland dry season. On the plus side, the location was secluded and very quiet. The only challenging things were the driveway because it is steep downhill from the road and the steps down to the cottage have no handrails, which my 88 year old mom would have needed. Nora was gracious, friendly, and very responsive.
Top Guest favourite
Guesthouse in Wilsonville
4.96 out of 5 average rating, 257 reviews

Creekside Haven

AnnaRating, 5 stars2 months ago
I had a great stay in Lois's guest house. Located alongside a beautiful creek the guesthouse was peaceful, comfortable and very conveniently located a few miles away from the local tec center. Lois was a very friendly and easy host to communicate with and I will certainly be staying here again in the future if in the area.

Guesthouses with a patio

Superhost
Guesthouse in Portland
5 out of 5 average rating, 102 reviews

Garden Home Getaway

EironRating, 5 stars2 weeks ago
The location was great! Quite neighborhood close to grocery stores and restaurants. The host was quick to respond to any questions. Nice location for a weekend getaway.
Superhost
Guesthouse in Sandy
4.96 out of 5 average rating, 75 reviews

Come Escape @ Mount Hood Retreat

LoganRating, 5 stars1 month ago
Beautiful place to stay! It was hard to tear myself away from sitting on the porch with the glorious view of Mt. Hood. Inside, the place is clutter-free/tidy, spacious, and cozy. Hosts provide clear and proactive instructions, I was always prepared with info about check-in and check-out with no confusion about the process. Fantastic location (in addition to the view) it provided a good balance of access to both Portland and the mountains/nature.
Superhost
Guesthouse in Molalla
5 out of 5 average rating, 39 reviews

A quiet retreat amongst the oaks

JacquelineRating, 5 stars4 months ago
We were welcomed with music and warmth as we stepped into Olesya's guest house. It was a great place to stay as we traveled to see different family members over the holidays. Olesya was very responsive and especially helpful after a power outage when the water pump needed to be reset early in the morning. My family would be excited to stay here again. Thank you Olesya!
Superhost
Guesthouse in Sherwood
4.99 out of 5 average rating, 141 reviews

Cozy Willamette Valley Cabin With Modern Comforts

DouglasRating, 5 stars3 weeks ago
Had an amazing stay at Jonathan’s cottage! It looked better than the pictures in person. Was super clean, comfortable, well appointed and in a great location. I highly recommend staying there, you will love it too!
Superhost
Guesthouse in West Linn
4.95 out of 5 average rating, 132 reviews

Charming one bedroom apartment in the forest.

JuanRating, 5 stars2 weeks ago
The area is beautiful, the Airbnb was amazing has everything you need for a nice and relaxing stay in Oregon.
Superhost
Guesthouse in Tigard
5 out of 5 average rating, 37 reviews

Furnished. Flicker Woods Guest House

TiaRating, 5 stars4 days ago
Loved the location of the property. It was literally in town minutes from all services - grocery, restaurants and everyday shopping, but had the best country living vibe. It is perfect for a single or couple. It was well stocked with everything you need. I would definitely stay here again!!
Superhost
Guesthouse in Happy Valley
4.96 out of 5 average rating, 79 reviews

Modern Private Guesthouse with Spacious Backyard

AnthonyRating, 5 stars6 months ago
Great stay! The place was clean and comfortable. Host was friendly and responsive. Loved the drive and the view!
Superhost
Guesthouse in Lake Oswego
4.9 out of 5 average rating, 21 reviews

{Lake Front Fun} The Little Cottage on West Bay

MaryRating, 5 stars5 months ago
This is a unique locale. It has the best equipped kitchen and supplies we have ever experienced in an Airbnb. We loved the decor of the kitchen like a cute 1950s diner. The shower was great. We visited in winter so we couldn’t take advantage of the wonderful water’s-edge outdoor living space. Jen is a great and instant communicator. We recommend you visit her!

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Lake Oswego
4.96 out of 5 average rating, 365 reviews

Cozy and Charming

KameshaRating, 5 stars2 weeks ago
Such a cozy and comfortable home! Everything was exactly as described, and we felt right at home. The attention to detail was really appreciated. Would love to stay again!
Top Guest favourite
Guesthouse in Portland
4.97 out of 5 average rating, 566 reviews

Dream Cottage! Springwater Bike/Walking Path!

MarthaRating, 5 stars1 week ago
Great spot for a night. Private and quiet. Everything was clean and well-organized. The kitchen had everything necessary for cooking and we were very comfortable.
Top Guest favourite
Guesthouse in Canby
4.95 out of 5 average rating, 199 reviews

Cozy Country Bungalow

BhavanRating, 5 stars6 months ago
If you're looking for country side house this is perfect place. Great property and my dog absolutely loved running around.
Top Guest favourite
Guesthouse in Lake Oswego
5 out of 5 average rating, 126 reviews

Oswego Empty Nest

kimRating, 5 stars3 weeks ago
The Empty Nest is my go-to in the Portland area. Robert is a great host with proactive communication. If there’s anything you need, he’s there. The place is comfortable and quiet. The kitchen is well equipped and stocked. It’s one of those places you can feel at home.
Guest favourite
Guesthouse in Milwaukie
4.91 out of 5 average rating, 57 reviews

Comfy-clean & Modern ADU

AmieRating, 5 stars1 month ago
The bathroom is definitely the centerpiece, with heated floors, a large walk in rain shower, makeup lighting on the mirror, and a full length mirror. The back patio is large and great for entertaining
Top Guest favourite
Guesthouse in Milwaukie
4.97 out of 5 average rating, 63 reviews

The Groovy Getaway

ManasaRating, 5 stars3 weeks ago
We enjoyed staying at Nikki’s place. The place was clean and tidy (exactly as shown in pictures). Our 1year old loved the private garden. We would love to stay here again if we are ever in the area
Top Guest favourite
Guesthouse in Milwaukie
4.97 out of 5 average rating, 58 reviews

Cozy Studio

JeffreyRating, 5 stars1 week ago
We felt very comfortable and safe. Very nice area and enjoyed my walks in the morning. We had a very private area for ourselves. We both work and were able to come and go as needed.
Top Guest favourite
Guesthouse in Damascus
4.98 out of 5 average rating, 81 reviews

Studio Cottage Perfect for Quiet Getaway

MikeRating, 5 stars1 month ago
Kara’s cottage was lovely! Very clean and well appointed. The location was easy to find and very private. Very comfortable and cozy for our late March stay. She gave great instructions and was quick to reply when we had questions.

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