
Guesthouse holiday rentals in Clackamas County
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Clackamas County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Clackamas County guesthouses
Family-Friendly guesthouses

Chayah House at Moriah Hills
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.

Andrew's House - Guest Suite
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.

Sellwood Luxury Studio Home
We loved our stay here in this beautiful neighborhood. Was perfect for our needs!

Secluded Willamette River Apartment in Lake Oswego
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!

Dancing Bear Cottage
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.

Cottage on the Creek in Lake Oswego
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.

Creekside Haven
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

Garden Home Getaway
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.

Come Escape @ Mount Hood Retreat
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.

A quiet retreat amongst the oaks
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!

Cozy Willamette Valley Cabin With Modern Comforts
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!

Charming one bedroom apartment in the forest.
The area is beautiful, the Airbnb was amazing has everything you need for a nice and relaxing stay in Oregon.

Furnished. Flicker Woods Guest House
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!!

Modern Private Guesthouse with Spacious Backyard
Great stay! The place was clean and comfortable. Host was friendly and responsive. Loved the drive and the view!

{Lake Front Fun} The Little Cottage on West Bay
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

Cozy and Charming
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!

Dream Cottage! Springwater Bike/Walking Path!
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.

Cozy Country Bungalow
If you're looking for country side house this is perfect place. Great property and my dog absolutely loved running around.

Oswego Empty Nest
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.

Comfy-clean & Modern ADU
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

The Groovy Getaway
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

Cozy Studio
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.

Studio Cottage Perfect for Quiet Getaway
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.
Destinations to explore
- Farmstay rentals Clackamas County
- Rentals with a hot tub Clackamas County
- Cottage rentals Clackamas County
- Rentals with pools Clackamas County
- Condo rentals Clackamas County
- Rentals with a fireplace Clackamas County
- Townhouse rentals Clackamas County
- House rentals Clackamas County
- Rentals with a washing machine and dryer Clackamas County
- Chalet rentals Clackamas County
- Waterfront rentals Clackamas County
- Rentals with lake access Clackamas County
- Rentals with breakfast Clackamas County
- Hotel rentals Clackamas County
- Fitness-friendly rentals Clackamas County
- Beachfront rentals Clackamas County
- Rentals with outdoor seating Clackamas County
- Rentals with a fire pit Clackamas County
- Rentals with a kayak Clackamas County
- Pet-friendly rentals Clackamas County
- Cabin rentals Clackamas County
- Kid-friendly rentals Clackamas County
- Apartment rentals Clackamas County
- Private suite rentals Clackamas County
- Ski-in/ski-out rentals Clackamas County
- Family-friendly rentals Clackamas County
- Rentals with a patio Clackamas County
- Guesthouse rentals Oregon
- Guesthouse rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Moda Center
- Silver Falls State Park
- Wooden Shoe Tulip Festival
- Timberline Lodge
- Mt. Hood Meadows
- Providence Park
- Oregon Zoo
- Oaks Bottom Wildlife Refuge
- Powell's City of Books
- Laurelhurst Park
- Mt. Hood Skibowl
- The Grotto
- Portland Japanese Garden
- Oaks Amusement Park
- Wonder Ballroom
- Hoyt Arboretum
- Domaine Serene
- Mission Theatre
- Beacon Rock State Park
- Bridal Veil Falls State Scenic Viewpoint
- Tryon Creek State Natural Area
- Stone Creek Golf Club
- Pittock Mansion
- Council Crest Park
- Things to do Clackamas County
- Food and drink Clackamas County
- Tours Clackamas County
- Nature and outdoors Clackamas County
- Art and culture Clackamas County
- Things to do Oregon
- Sports activities Oregon
- Food and drink Oregon
- Entertainment Oregon
- Art and culture Oregon
- Tours Oregon
- Sightseeing Oregon
- Wellness Oregon
- Nature and outdoors Oregon
- Things to do United States
- Sightseeing United States
- Wellness United States
- Nature and outdoors United States
- Tours United States
- Food and drink United States
- Sports activities United States
- Art and culture United States
- Entertainment United States